Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Benzoic Acid | HCID 243 | — |
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate | HCID 2733207 | — |
| Reactant | HCID 66915521 | HCID 66915521 | — |
| Product | HCID 57960889 | HCID 57960889 | — |
Reaction Steps
A mixture of 3-cyclobutyl-1-(1,2,3,6-tetrahydropyridin-4-yl)-imidazo[1,5-a]pyrazin-8-ylamine (20.0 mg, 0.0742 mmol), benzoic acid (9.97 mg, 0.0817 mmol), TBTU (47.7 mg, 0.148 mmol), DIEA (0.0647 mL, 0.371 mmol) and DMF (1 mL, 0.01 mol) was stirred at rt for 10 min. The reaction mixture was directly given for Gilson HPLC purification. The fractions containing the pure product were collected and concentrated in vacuo to afford the title compound as a yellow solid. 1H NMR (400 MHz, CDCl3): δ=1.96-2.06 (m, 1H) 2.09-2.23 (m, 1H) 2.40-2.63 (m, 4H) 2.72-2.93 (m, 2H) 3.57-3.88 (m, 3H) 3.98-4.34 (m, 1H) 4.47 (br. s., 1H) 5.13-5.45 (m, 2H) 5.72-6.14 (m, 1H) 7.04-7.08 (m, 2H) 7.42-7.51 (m, 5H). MS (ES+): m/z 374.07 (100) [MH+]. HPLC: tR=2.13 min (polar—5 min).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08481733B2 |
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| Source dataset | uspto-grants-2013_07 |
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| ORD ID | ord-89bf9f4781b24933b1b29cd4b4d2d85d |
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| Source note | uspto-grants-2013_07 |
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