Hydrochloric Acid → 7-(3-Aminophenyl)-2-(4-phenoxyphenyl)pyrazolo[1,5-a]pyrimidine-3-carbonitrile

HRID 64259Notes

Reaction equation

[C:1]([C:3]1[C:4]([C:22]2[CH:27]=[CH:26][C:25]([O:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[CH:24][CH:23]=2)=[N:5][N:6]2[C:11]([C:12]3[CH:13]=[C:14]([NH:18]C(=O)C)[CH:15]=[CH:16][CH:17]=3)=[CH:10][CH:9]=[N:8][C:7]=12)#[N:2].Cl>C(O)C>[NH2:18][C:14]1[CH:13]=[C:12]([C:11]2[N:6]3[N:5]=[C:4]([C:22]4[CH:27]=[CH:26][C:25]([O:28][C:29]5[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=5)=[CH:24][CH:23]=4)[C:3]([C:1]#[N:2])=[C:7]3[N:8]=[CH:9][CH:10]=2)[CH:17]=[CH:16][CH:15]=1

Participants

Conditions

Temperature: 75 °C

Procedure

To a solution of N-(3-(3-cyano-2-(4-phenoxyphenyl)pyrazolo[1,5-a]pyrimidin-7-yl)phenyl)acetamide (285 mg, 0.64 mmol) in ethanol (6 mL) was added HCl (3 mL). The mixture stirred at 75° C. for 3 hr. Concentrated to afford 250 mg (97%) of 7-(3-aminophenyl)-2-(4-phenoxyphenyl)pyrazolo[1,5-a]pyrimidine-3-carbonitrile as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ 8.90 (d, J=4.4 Hz, 1H), 8.67 (br s, 2H), 8.15 (d, J=8.8 Hz, 2H), 8.06 (s, 1H), 7.87 (d, J=8.0 Hz, 1H), 7.64 (t, J=8.0 Hz, 1H), 7.57 (d, J=4.4 Hz, 1H), 7.48-7.44 (m, 3H), 7.25-7.18 (m, 3H), 7.13 (d, J=8.0 Hz, 2H). MS (ESI) m/e [M+1]+ 404.

Workup

concentrationConcentrated

Sources & evidence

ORD record: ord-2e62c9b8a7b44fdd9748764df2d274ef
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09447106B2

Reaction notes

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