Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Trifluoroacetic acid | HCID 6422 | — |
| Reactant | tert-Butyl (1S,2R)-2-(4-(1-(difluoromethyl)-1H-pyrazol-4-yl)-2-(2,4-dimethoxybenzyl)-7-fluoro-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-6-ylamino)cyclohexylcarbamate | HCID 86654725 | — |
| Product | Trifluoroacetic acid | HCID 6422 | 86% |
| Product | 6-((1R,2S)-2-Aminocyclohexylamino)-4-(1-(difluoromethyl)-1H-pyrazol-4-yl)-7-fluoro-1H-pyrrolo[3,4-c]pyridin-3(2H)-one | HCID 53250369 | — |
Reaction Steps
A solution of tert-butyl (1S,2R)-2-(4-(1-(difluoromethyl)-1H-pyrazol-4-yl)-2-(2,4-dimethoxybenzyl)-7-fluoro-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-6-ylamino)cyclohexylcarbamate (36 mg, 0.057 mmol) in TFA (2 mL) was heated at 60° C. for 2 h. After removal of the solvent, the residue was diluted in MeOH (2 mL) and was purified by preparative HPLC. The fractions were collected and stripped to dryness via rotary evaporation to yield the title compound as a TFA salt (18.7 mg, 86%). 1H NMR (500 MHz, DMSO-d6) δ ppm 1.40-1.52 (m, 2H), 1.58-1.76 (m, 3H), 1.75-1.94 (m, 3H), 3.67 (br s, 1H), 4.44 (d, J=4.88 Hz, 2H), 4.53 (br s, 1H), 6.86 (d, J=6.83 Hz, 1H), 7.71 (br s, 2H), 7.79-8.12 (m, 1H), 8.53 (s, 2H), 9.41 (s, 1H). [M+H] calc'd for C17H19F3N6O, 381. found, 381.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08440689B2 |
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| Source dataset | uspto-grants-2013_05 |
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| ORD ID | ord-05a1b1bc143a4fdcb9d9a26ac353303f |
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| Source note | uspto-grants-2013_05 |
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