4-(Trifluoromethyl)benzenecarbothioyl chloride → HCID 86625580, compound

HRID 70978Notes

Reaction equation

HRID 70978 reaction equation
[NH2:1][C:2]([CH3:19])([CH2:5][N:6]1[C:14]([O:15][CH2:16][CH3:17])=[C:13]2[C:8]([CH:9]=[CH:10][C:11]([Cl:18])=[CH:12]2)=[N:7]1)[C:3]#[N:4].[F:20][C:21]([F:32])([F:31])[C:22]1[CH:30]=[CH:29][C:25]([C:26](Cl)=[S:27])=[CH:24][CH:23]=1>>[Cl:18][C:11]1[CH:10]=[CH:9][C:8]2[C:13](=[C:14]([O:15][CH2:16][CH3:17])[N:6]([CH2:5][C:2]([NH:1][C:26](=[S:27])[C:25]3[CH:24]=[CH:23][C:22]([C:21]([F:20])([F:31])[F:32])=[CH:30][CH:29]=3)([C:3]#[N:4])[CH3:19])[N:7]=2)[CH:12]=1

Participants

3

Reactant 2

HCID 198624844-(Trifluoromethyl)benzenecarbothioyl chlorideHCID 666209622-amino-3-(5-chloro-3-ethoxy-2H-indazol-2-yl)-2-methylpropionitrile

Product 1

HCID 86625580HCID 86625580, compound

Procedure

Using a procedure similar to that described in Example 1, except using 2-amino-3-(5-chloro-3-ethoxy-2H-indazol-2-yl)-2-methylpropionitrile (52 mg, described in Example 109) and 4-trifluoromethylthiobenzoyl chloride, the title compound was isolated as a white solid (83 mg, 93%). MS (ES): M/Z [M+H]=483. 1H NMR: (400 MHz, DMSO-d6): 1.26 (t, J=7.0 Hz, 3H), 1.71 (s, 3H), 4.52 (q, J=7.0 Hz, 2H), 4.78 (d, 1H), 4.93 (d, 1H), 7.16 (dd, J=9.3, 1.9 Hz, 1H), 7.47 (d, J=9.3 Hz, 1H), 7.85-7.89 (m, 3H), 7.96 (d, J=8.8 Hz, 2H) and 8.99 (s, 1H). 19F NMR (376 MHz, DMSO-d6): −42.0 (s, 3F).

Sources & evidence

ORD record
ord-ab4654aaf6634015a2a83ea6f2492d93
Source dataset
uspto-grants-2014_09
Patent number
US08822689B2

Reaction notes

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