4-(Trifluoromethyl)benzenecarbothioyl chloride → HCID 86641839, compound

HRID 1257068Notes

Reaction equation

HRID 1257068 reaction equation
[NH2:1][C:2]([CH3:16])([CH2:5][N:6]1[CH:14]=[C:13]2[C:8]([C:9]([Br:15])=[N:10][CH:11]=[CH:12]2)=[N:7]1)[C:3]#[N:4].[F:17][C:18]([F:29])([F:28])[C:19]1[CH:27]=[CH:26][C:22]([C:23](Cl)=[S:24])=[CH:21][CH:20]=1>>[Br:15][C:9]1[C:8]2=[N:7][N:6]([CH2:5][C:2]([NH:1][C:23](=[S:24])[C:22]3[CH:21]=[CH:20][C:19]([C:18]([F:17])([F:28])[F:29])=[CH:27][CH:26]=3)([C:3]#[N:4])[CH3:16])[CH:14]=[C:13]2[CH:12]=[CH:11][N:10]=1

Participants

3

Reactant 2

HCID 198624844-(Trifluoromethyl)benzenecarbothioyl chlorideHCID 86641840HCID 86641840, compound

Product 1

HCID 86641839HCID 86641839, compound

Procedure

Using a procedure similar to that described in Example 1, except using 2-amino-3-(7-bromo-2H-pyrazolo[3,4-c]pyridin-2-yl)-2-methylpropionitrile (100 mg, described in Example 202) and 4-trifluoromethylthiobenzoyl chloride (93 mg), the title compound was isolated as a white solid (153 mg, 89%). Rf=0.25 (1:1 EA/heptane). MS (ES): M/Z [M+H]=484. 1H NMR: (400 MHz, DMSO-d6): 1.70 (s, 3H), 5.18 (d, J=13.5 Hz, 1H), 5.33 (d, J=13.5 Hz, 1H), 7.76 (d, J=5.8 Hz, 1H), 7.87-7.90 (m, 3H), 7.96 (d, J=8.4 Hz, 1H), 8.71 (s 1H) and 9.01 (d, J=1.1 Hz, 1H). 19F NMR (376 MHz, DMSO-d6): −42.0 (s, 3F).

Sources & evidence

ORD record
ord-ee49cb9af4a84849966be0aa3ba7de86
Source dataset
uspto-grants-2013_06
Patent number
US08461176B2

Reaction notes

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