Hydrochloric Acid → N-(3-(5-cyano-2-methoxyphenyl)-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide

HRID 1466630Notes

Reaction equation

[C:1]([C:3]1[CH:4]=[CH:5][C:6]([O:34][CH3:35])=[C:7]([C:9]2[N:13](CCOC[Si](C)(C)C)[N:12]=[CH:11][C:10]=2[NH:22][C:23]([C:25]2[CH:26]=[N:27][N:28]3[CH:33]=[CH:32][CH:31]=[N:30][C:29]=23)=[O:24])[CH:8]=1)#[N:2].Cl>C(O)C.O>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([O:34][CH3:35])=[C:7]([C:9]2[NH:13][N:12]=[CH:11][C:10]=2[NH:22][C:23]([C:25]2[CH:26]=[N:27][N:28]3[CH:33]=[CH:32][CH:31]=[N:30][C:29]=23)=[O:24])[CH:8]=1)#[N:2]

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of N-(5-(5-cyano-2-methoxyphenyl)-1-(2-((trimethylsilyl)methoxy)ethyl)-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide (1.0 g, 2.04 mmol) in 20 mL ethanol was added HCl (2.0 mL of a 6 M solution in water, 12 mmol). The reaction mixture was then stirred at 70° C. for 4 hours. After cooling to room temperature, a light yellow precipitate formed, which was filtered off and rinsed with methanol and diethyl ether. The filtrate was reduced in volume to precipitate more solid product, which was filtered off. The combined collected solids were dried under vacuum to yield 530 mg (72%) of N-(5-(5-cyano-2-methoxyphenyl)-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide. LCMS (ESI) m+H=360.1; 1H NMR (400 MHz, DMSO-d6) δ12.98 (s, 1H), 9.59 (s, 1H), 9.30 (dd, 1H), 8.73 (d, 1H), 8.61 (s, 1H), 8.23 (s, 1H), 8.22 (s, 1H), 7.78 (s, 1H), 7.43 (d, 1H), 7.25 (s, 1H), 3.9 (s, 3H).

Workup

temperatureAfter cooling to room temperature
customa light yellow precipitate formed
filtrationwhich was filtered off
washrinsed with methanol and diethyl ether
customto precipitate more solid product, which
filtrationwas filtered off
customThe combined collected solids
customwere dried under vacuum

Sources & evidence

ORD record: ord-87a5b881dba24ea3bdb75dccf16df62a
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08999998B2

Reaction notes

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