4-(Trifluoromethyl)benzenecarbothioyl chloride → HCID 86641833, compound

HRID 1257064Notes

Reaction equation

HRID 1257064 reaction equation
[NH2:1][C:2]([CH3:17])([CH2:5][N:6]1[CH:16]=[C:9]2[N:10]=[C:11]([Br:15])[C:12]([Br:14])=[CH:13][C:8]2=[N:7]1)[C:3]#[N:4].[F:18][C:19]([F:30])([F:29])[C:20]1[CH:28]=[CH:27][C:23]([C:24](Cl)=[S:25])=[CH:22][CH:21]=1>>[C:3]([C:2]([NH:1][C:24](=[S:25])[C:23]1[CH:22]=[CH:21][C:20]([C:19]([F:18])([F:29])[F:30])=[CH:28][CH:27]=1)([CH3:17])[CH2:5][N:6]1[CH:16]=[C:9]2[N:10]=[C:11]([Br:15])[C:12]([Br:14])=[CH:13][C:8]2=[N:7]1)#[N:4]

Participants

3

Reactant 2

HCID 198624844-(Trifluoromethyl)benzenecarbothioyl chlorideHCID 86641834HCID 86641834, compound

Product 1

HCID 86641833HCID 86641833, compound

Procedure

Using a procedure similar to that described in Example 1, except using 2-amino-3-(5,6-dibromo-2H-pyrazolo[4,3-b]pyridin-2-yl)-2-methylpropionitrile (60 mg, described in Example 195) and 4-trifluoromethylthiobenzoyl chloride (28 μL), the title compound was isolated as a white solid (44 mg, 47%). MS (ES): M/Z [M+H]=562. 1H NMR: (400 MHz, DMSO-d6): 1.68 (s, 3H), 5.13 (d, J=13.2 Hz, 1H), 5.18 (d, J=13.2 Hz, 1H), 7.88 (d, J=8.4 Hz, 2H), 7.94 (d, J=8.4 Hz, 2H), 8.74 (s, 1H), 8.79 (s, 1H) and 9.04 (s, 1H). 19F NMR (376 MHz, DMSO-d6): −41.9 (s, 3F).

Sources & evidence

ORD record
ord-d6b107a63a72499b9f927aea33ff38e9
Source dataset
uspto-grants-2013_06
Patent number
US08461176B2

Reaction notes

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