4-(Trifluoromethyl)benzenecarbothioyl chloride → HCID 86641832, compound

HRID 1257062Notes

Reaction equation

HRID 1257062 reaction equation
[NH2:1][C:2]([CH3:18])([CH2:5][N:6]1[CH:17]=[C:9]2[N:10]=[C:11]([O:15][CH3:16])[C:12]([Br:14])=[CH:13][C:8]2=[N:7]1)[C:3]#[N:4].[F:19][C:20]([F:31])([F:30])[C:21]1[CH:29]=[CH:28][C:24]([C:25](Cl)=[S:26])=[CH:23][CH:22]=1>>[Br:14][C:12]1[C:11]([O:15][CH3:16])=[N:10][C:9]2=[CH:17][N:6]([CH2:5][C:2]([NH:1][C:25](=[S:26])[C:24]3[CH:23]=[CH:22][C:21]([C:20]([F:19])([F:30])[F:31])=[CH:29][CH:28]=3)([C:3]#[N:4])[CH3:18])[N:7]=[C:8]2[CH:13]=1

Participants

3

Reactant 2

HCID 198624844-(Trifluoromethyl)benzenecarbothioyl chlorideHCID 68707362HCID 68707362, compound

Product 1

HCID 86641832HCID 86641832, compound

Procedure

Using a procedure similar to that described in Example 1, except using 2-amino-3-(6-bromo-5-methoxy-2H-pyrazolo[4,3-b]pyridin-2-yl)-2-methylpropionitrile (100 mg described in Example 193) and 4-trifluoromethylthiobenzoyl chloride, the title compound was isolated as a white solid (67.5 mg, 41%). MS (ES): M/Z [M+H]=514. 1H NMR: (400 MHz, CHLOROFORM-d): 1.93 (s, 3H), 4.05 (s, 3H), 4.76 (d, J=14.4 Hz, 1H), 4.90 (d, J=14.4 Hz, 1H), 7.78 (d, J=8.6 Hz, 2H), 7.87 (d, J=8.6 Hz, 2H), 8.12 (s, 1H) and 8.20 (s, 2H). 19F NMR (376 MHz, CHLOROFORM-d): −42.2 (s, 3F).

Sources & evidence

ORD record
ord-a694dd2c10bf42d782db31a0c29d45f4
Source dataset
uspto-grants-2013_06
Patent number
US08461176B2

Reaction notes

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