4-(Trifluoromethyl)benzenecarbothioyl chloride → HCID 86641837, compound

HRID 1257067Notes

Reaction equation

HRID 1257067 reaction equation
[NH2:1][C:2]([CH3:16])([CH2:5][N:6]1[CH:14]=[C:13]2[C:8]([CH:9]=[N:10][C:11]([Br:15])=[CH:12]2)=[N:7]1)[C:3]#[N:4].[F:17][C:18]([F:29])([F:28])[C:19]1[CH:27]=[CH:26][C:22]([C:23](Cl)=[S:24])=[CH:21][CH:20]=1>>[Br:15][C:11]1[N:10]=[CH:9][C:8]2=[N:7][N:6]([CH2:5][C:2]([NH:1][C:23](=[S:24])[C:22]3[CH:21]=[CH:20][C:19]([C:18]([F:17])([F:28])[F:29])=[CH:27][CH:26]=3)([C:3]#[N:4])[CH3:16])[CH:14]=[C:13]2[CH:12]=1

Participants

3

Reactant 2

HCID 198624844-(Trifluoromethyl)benzenecarbothioyl chlorideHCID 86641838HCID 86641838, compound

Product 1

HCID 86641837HCID 86641837, compound

Procedure

Using a procedure similar to that described in Example 1, except using 2-amino-3-(5-bromo-2H-pyrazolo[3,4-c]pyridin-2-yl)-2-methylpropionitrile (100 mg, described in Example 199) and 4-trifluoromethylthiobenzoyl chloride (92 mg), the title compound was isolated as a white solid (150 mg, 87%). MS (ES): M/Z [M+H]=484. 1H NMR: (400 MHz, DMSO-d6): 1.69 (s, 3H), 5.20 (d, J=13.5 Hz, 1H), 5.27 (d, J=13.5 Hz, 1H), 7.88 (d, J=8.4 Hz, 2H), 7.93 (d, J=8.4 Hz, 2H), 8.04 (d, J=1.2 Hz, 1H), 8.54 (d, J=0.6 Hz, 1H) and 9.05 (d, J=1.1 Hz, 1H). 19F NMR (376 MHz, DMSO-d6): −41.9 (s, 3F).

Sources & evidence

ORD record
ord-6bee6b9b752d44149c822ebfab95cfb1
Source dataset
uspto-grants-2013_06
Patent number
US08461176B2

Reaction notes

Loading…