4-(Trifluoromethyl)benzenecarbothioyl chloride → HCID 86625574, compound

HRID 70970Notes

Reaction equation

HRID 70970 reaction equation
[NH2:1][C:2]([CH3:18])([CH2:5][N:6]1[CH:14]=[C:13]2[C:8]([CH:9]=[CH:10][C:11]([N+:15]([O-:17])=[O:16])=[CH:12]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>>[C:3]([C:2]([NH:1][C:25](=[S:26])[C:24]1[CH:23]=[CH:22][C:21]([C:20]([F:19])([F:30])[F:31])=[CH:29][CH:28]=1)([CH3:18])[CH2:5][N:6]1[CH:14]=[C:13]2[C:8]([CH:9]=[CH:10][C:11]([N+:15]([O-:17])=[O:16])=[CH:12]2)=[N:7]1)#[N:4]

Participants

3

Reactant 2

HCID 198624844-(Trifluoromethyl)benzenecarbothioyl chlorideHCID 666209372-amino-2-methyl-3-(5-nitro-2H-indazol-2-yl)propionitrile

Product 1

HCID 86625574HCID 86625574, compound

Procedure

Using a procedure similar to that described in Example 1, except using 2-amino-2-methyl-3-(5-nitro-2H-indazol-2-yl)propionitrile (62 mg, described in Example 96) and 4-trifluoromethylthiobenzoyl chloride, the title compound was isolated as a white solid (96 mg, 84%). MS (ES): M/Z [M+H]=450. 1H NMR: (400 MHz, DMSO-d6): 1.72 (s, 3H), 5.22 (q, 2H), 7.81 (d, J=9.5 Hz, 1H), 7.86-7.90 (m, 2H), 7.92-7.97 (m, 2H), 8.00-8.05 (m, 1H), 8.83 (s, 1H), 8.95 (d, J=1.9 Hz, 1H) and 9.07 (s, 1H). 19F NMR (376 MHz, DMSO-d6): −41.9 (s, 3F).

Sources & evidence

ORD record
ord-c46a081d5cf74b44a79af18b66ffae4d
Source dataset
uspto-grants-2014_09
Patent number
US08822689B2

Reaction notes

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