4-(Trifluoromethyl)benzenecarbothioyl chloride → HCID 86625584, compound

HRID 70983Notes

Reaction equation

HRID 70983 reaction equation
[NH2:1][C:2]([CH3:21])([CH2:5][N:6]1[C:14]([O:15][CH3:16])=[C:13]2[C:8]([CH:9]=[C:10]([C:17]([F:20])([F:19])[F:18])[CH:11]=[CH:12]2)=[N:7]1)[C:3]#[N:4].[F:22][C:23]([F:34])([F:33])[C:24]1[CH:32]=[CH:31][C:27]([C:28](Cl)=[S:29])=[CH:26][CH:25]=1>>[C:3]([C:2]([NH:1][C:28](=[S:29])[C:27]1[CH:26]=[CH:25][C:24]([C:23]([F:22])([F:33])[F:34])=[CH:32][CH:31]=1)([CH3:21])[CH2:5][N:6]1[C:14]([O:15][CH3:16])=[C:13]2[C:8]([CH:9]=[C:10]([C:17]([F:19])([F:20])[F:18])[CH:11]=[CH:12]2)=[N:7]1)#[N:4]

Participants

3

Reactant 2

HCID 198624844-(Trifluoromethyl)benzenecarbothioyl chlorideHCID 666206332-amino-3-(3-methoxy-6-trifluoromethyl-2H-indazol-2-yl)-2-methylpropionitrile

Product 1

HCID 86625584HCID 86625584, compound

Procedure

Using a procedure similar to that described in Example 1, except using 2-amino-3-(3-methoxy-6-trifluoromethyl-2H-indazol-2-yl)-2-methylpropionitrile (50 mg, described in Example 120) and 4-trifluoromethylthiobenzoyl chloride, the title compound was isolated as a white solid (66 mg, 78%). MS (ES): M/Z [M+H]=503. 1H NMR: (400 MHz, DMSO-d6): 1.72 (s, 3H), 4.24 (s, 3H), 4.84 (d, J=13.8 Hz, 1H), 4.96 (d, J=13.9 Hz, 1H), 7.08 (dd, J=9.0, 1.4 Hz, 1H), 7.85 (s, 1H), 7.88 (d, J=8.2 Hz, 2H), 7.94-7.99 (m, 2H), 8.09 (d, J=9.0 Hz, 1H) and 8.99 (s, 1H). 19F NMR (376 MHz, DMSO-d6): −42.0 (s, 3F) and −61.8 (s, 3F).

Sources & evidence

ORD record
ord-a0f148fd76304bc9878e4e4e2eddebbf
Source dataset
uspto-grants-2014_09
Patent number
US08822689B2

Reaction notes

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