4-(Trifluoromethyl)benzenecarbothioyl chloride → HCID 86625586, compound

HRID 415772Notes

Reaction equation

HRID 415772 reaction equation
[NH2:1][C:2]([CH3:20])([CH2:5][N:6]1[C:14]([O:15][CH2:16][CH2:17][CH3:18])=[C:13]2[C:8]([CH:9]=[C:10]([Cl:19])[CH:11]=[CH:12]2)=[N:7]1)[C:3]#[N:4].[F:21][C:22]([F:33])([F:32])[C:23]1[CH:31]=[CH:30][C:26]([C:27](Cl)=[S:28])=[CH:25][CH:24]=1>>[Cl:19][C:10]1[CH:11]=[CH:12][C:13]2[C:8]([CH:9]=1)=[N:7][N:6]([CH2:5][C:2]([NH:1][C:27](=[S:28])[C:26]1[CH:25]=[CH:24][C:23]([C:22]([F:21])([F:32])[F:33])=[CH:31][CH:30]=1)([C:3]#[N:4])[CH3:20])[C:14]=2[O:15][CH2:16][CH2:17][CH3:18]

Participants

3

Reactant 2

HCID 198624844-(Trifluoromethyl)benzenecarbothioyl chlorideHCID 66620766HCID 66620766, compound

Product 1

HCID 86625586HCID 86625586, compound

Procedure

Using a procedure similar to that described in Example 1, except using 2-amino-3-(6-chloro-3-propoxy-2H-indazol-2-yl)-2-methylpropionitrile (104 mg, described in Example 124) and 4-trifluoromethylthiobenzoyl chloride, the title compound was isolated as a white solid (88 mg, 46%). MS (ES): M/Z [M+H]=497. 1H NMR: (400 MHz, CHLOROFORM-d): 1.14 (t, J=7.4 Hz, 3H), 1.90 (s, 3H), 1.92-2.04 (m, 2H), 4.51 (d, J=14.2 Hz, 1H), 4.56-4.70 (m, 2H), 4.82 (d, J=14.2 Hz, 1H), 6.92 (dd, J=9.1, 1.7 Hz, 1H), 7.47 (d, J=1.7 Hz, 1H), 7.62 (dd, J=9.1, 0.5 Hz, 1H), 7.79 (dd, J=8.3 Hz, 2H), 7.91-7.99 (m, 2H) and 9.17 (s, 1H). 19F NMR (376 MHz, CHLOROFORM-d): −42.3 (s, 3F).

Sources & evidence

ORD record
ord-0fa5121c05004856956e863463fb8944
Source dataset
uspto-grants-2012_01
Patent number
US08088801B2

Reaction notes

Loading…