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Issue in honor of Professor Girolamo (Gilmo) Cirrincione ARKIVOC 2022, ii, S1-S21 Page S1 © AUTHOR(S) Supplementary Material Synthesis of pyrazolo[1,5-a]pyrimidine ring as a possible bioisosteric replacement of the 5-(1H-pyrrol-1-yl)pyrazole scaffold Claudia Mugnaini, Livia Pasculini, Carlotta Pagli, Antonella Brizzi, Marco Paolino, Beatrice Gianibbi, and Federico Corelli* Department of Biotechnology, Chemistry and Pharmacy, University of Siena, 53100 Siena, Italy Email: [email protected] Table of Contents HPLC/MS traces for compounds 2a-f Compound 2a......................................................................................................................................................... S2 Compound 2b......................................................................................................................................................... S4 Compound 2c ......................................................................................................................................................... S6 Compound 2d......................................................................................................................................................... S8 Compound 2e....................................................................................................................................................... S10 Compound 2f ....................................................................................................................................................... S12 13 C NMR spectra of compounds 4,5 and 2a-f Compound 4......................................................................................................................................................... S14 Compound 5......................................................................................................................................................... S15 Compound 2a....................................................................................................................................................... S16 Compound 2b....................................................................................................................................................... S17 Compound 2c ....................................................................................................................................................... S18 Compound 2d....................................................................................................................................................... S19 Compound 2e....................................................................................................................................................... S20 Compound 2f ....................................................................................................................................................... S21

Supplementary Material Synthesis of pyrazolo[1,5-a

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Page 1: Supplementary Material Synthesis of pyrazolo[1,5-a

Issue in honor of Professor Girolamo (Gilmo) Cirrincione ARKIVOC 2022, ii, S1-S21

Page S1 ©AUTHOR(S)

Supplementary Material

Synthesis of pyrazolo[1,5-a]pyrimidine ring as a possible bioisosteric replacement of the 5-(1H-pyrrol-1-yl)pyrazole scaffold

Claudia Mugnaini, Livia Pasculini, Carlotta Pagli, Antonella Brizzi, Marco Paolino, Beatrice Gianibbi, and Federico Corelli*

Department of Biotechnology, Chemistry and Pharmacy, University of Siena, 53100 Siena, Italy

Email: [email protected]

Table of Contents HPLC/MS traces for compounds 2a-f

Compound 2a ......................................................................................................................................................... S2

Compound 2b......................................................................................................................................................... S4

Compound 2c ......................................................................................................................................................... S6

Compound 2d......................................................................................................................................................... S8

Compound 2e ....................................................................................................................................................... S10

Compound 2f ....................................................................................................................................................... S12 13C NMR spectra of compounds 4,5 and 2a-f

Compound 4 ......................................................................................................................................................... S14

Compound 5 ......................................................................................................................................................... S15

Compound 2a ....................................................................................................................................................... S16

Compound 2b....................................................................................................................................................... S17

Compound 2c ....................................................................................................................................................... S18

Compound 2d....................................................................................................................................................... S19

Compound 2e ....................................................................................................................................................... S20

Compound 2f ....................................................................................................................................................... S21

mailto:[email protected]
Page 2: Supplementary Material Synthesis of pyrazolo[1,5-a

Issue in honor of Professor Girolamo (Gilmo) Cirrincione ARKIVOC 2022, ii, S1-S21

Page S2 ©AUTHOR(S)

Page 3: Supplementary Material Synthesis of pyrazolo[1,5-a

Issue in honor of Professor Girolamo (Gilmo) Cirrincione ARKIVOC 2022, ii, S1-S21

Page S3 ©AUTHOR(S)

Page 4: Supplementary Material Synthesis of pyrazolo[1,5-a

Issue in honor of Professor Girolamo (Gilmo) Cirrincione ARKIVOC 2022, ii, S1-S21

Page S4 ©AUTHOR(S)

Page 5: Supplementary Material Synthesis of pyrazolo[1,5-a

Issue in honor of Professor Girolamo (Gilmo) Cirrincione ARKIVOC 2022, ii, S1-S21

Page S5 ©AUTHOR(S)

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Issue in honor of Professor Girolamo (Gilmo) Cirrincione ARKIVOC 2022, ii, S1-S21

Page S6 ©AUTHOR(S)

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Issue in honor of Professor Girolamo (Gilmo) Cirrincione ARKIVOC 2022, ii, S1-S21

Page S7 ©AUTHOR(S)

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Issue in honor of Professor Girolamo (Gilmo) Cirrincione ARKIVOC 2022, ii, S1-S21

Page S8 ©AUTHOR(S)

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Issue in honor of Professor Girolamo (Gilmo) Cirrincione ARKIVOC 2022, ii, S1-S21

Page S9 ©AUTHOR(S)

Page 10: Supplementary Material Synthesis of pyrazolo[1,5-a

Issue in honor of Professor Girolamo (Gilmo) Cirrincione ARKIVOC 2022, ii, S1-S21

Page S10 ©AUTHOR(S)

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Issue in honor of Professor Girolamo (Gilmo) Cirrincione ARKIVOC 2022, ii, S1-S21

Page S11 ©AUTHOR(S)

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Issue in honor of Professor Girolamo (Gilmo) Cirrincione ARKIVOC 2022, ii, S1-S21

Page S12 ©AUTHOR(S)

Page 13: Supplementary Material Synthesis of pyrazolo[1,5-a

Issue in honor of Professor Girolamo (Gilmo) Cirrincione ARKIVOC 2022, ii, S1-S21

Page S13 ©AUTHOR(S)

Page 14: Supplementary Material Synthesis of pyrazolo[1,5-a

Issue in honor of Professor Girolamo (Gilmo) Cirrincione ARKIVOC 2022, ii, S1-S21

Page S14 ©AUTHOR(S)

13C DEPT (CDCl3, 600 MHz) of compound 4.

Page 15: Supplementary Material Synthesis of pyrazolo[1,5-a

Issue in honor of Professor Girolamo (Gilmo) Cirrincione ARKIVOC 2022, ii, S1-S21

Page S15 ©AUTHOR(S)

13C DEPT (CDCl3, 600 MHz) of compound 5.

Page 16: Supplementary Material Synthesis of pyrazolo[1,5-a

Issue in honor of Professor Girolamo (Gilmo) Cirrincione ARKIVOC 2022, ii, S1-S21

Page S16 ©AUTHOR(S)

13C NMR (CDCl3, 400 MHz) of compound 2a.

Page 17: Supplementary Material Synthesis of pyrazolo[1,5-a

Issue in honor of Professor Girolamo (Gilmo) Cirrincione ARKIVOC 2022, ii, S1-S21

Page S17 ©AUTHOR(S)

13C NMR (CDCl3, 400 MHz) of compound 2b

Page 18: Supplementary Material Synthesis of pyrazolo[1,5-a

Issue in honor of Professor Girolamo (Gilmo) Cirrincione ARKIVOC 2022, ii, S1-S21

Page S18 ©AUTHOR(S)

13C NMR (DMSO-d6, 400 MHz) of compound 2c.

Page 19: Supplementary Material Synthesis of pyrazolo[1,5-a

Issue in honor of Professor Girolamo (Gilmo) Cirrincione ARKIVOC 2022, ii, S1-S21

Page S19 ©AUTHOR(S)

13C NMR (DMSO-d6, 400 MHz) of compound 2d.

Page 20: Supplementary Material Synthesis of pyrazolo[1,5-a

Issue in honor of Professor Girolamo (Gilmo) Cirrincione ARKIVOC 2022, ii, S1-S21

Page S20 ©AUTHOR(S)

13C NMR (DMSO-d6, 400 MHz) of compound 2e.

Page 21: Supplementary Material Synthesis of pyrazolo[1,5-a

Issue in honor of Professor Girolamo (Gilmo) Cirrincione ARKIVOC 2022, ii, S1-S21

Page S21 ©AUTHOR(S)

13C NMR (CDCl3, 400 MHz) of compound 2f.


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