HCID 18537360, compound → HCID 86583817, compound

HRID 2298616Notes

Reaction equation

HRID 2298616 reaction equation
[NH2:1][C:2](=[S:13])[C:3]1[CH:4]=[C:5]([C:9]([O:11][CH3:12])=[S:10])[S:6][C:7]=1[CH3:8].[F:14][C:15]([F:32])([F:31])[C:16]1[CH:17]=[C:18]([C:26](=O)[CH:27](Br)[CH3:28])[CH:19]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:21]=1>>[F:14][C:15]([F:31])([F:32])[C:16]1[CH:17]=[C:18]([C:26]2[N:1]=[C:2]([C:3]3[CH:4]=[C:5]([C:9]([O:11][CH3:12])=[S:10])[S:6][C:7]=3[CH3:8])[S:13][C:27]=2[CH3:28])[CH:19]=[C:20]([C:22]([F:23])([F:24])[F:25])[CH:21]=1

Participants

3

Reactant 2

HCID 18537360HCID 18537360, compoundHCID 86583815Methyl 4-(aminothioxomethyl)-5-methylthiothiophene-2-carboxylate

Product 1

HCID 86583817HCID 86583817, compound

Procedure

A solution of 75 mg (0.3 mmol) of methyl 4-(aminothioxomethyl)-5-methylthiothiophene-2-carboxylate (Maybridge, Cornwall, UK) was reacted with 105 mg 1-[3,5-Bis(trifluoromethyl)phenyl]-2-bromopropan-1-one in a manner similar to Example 8, step (a) to give, after preparative thin-layer chromatrography purification, methyl 4-{4-[3,5-bis(trifluoromethyl)phenyl]-5-methyl(1,3-thiazol-2-yl)}-5-methylthiothiophene-2-carboxylate (16.2 mg, 11%) as a solid. 1H-NMR (DMSO-d6; 300 MHz) δ8.41 (m, 2H), 8.18 (m, 2H), 3.86 (s, 3H), 2.75 (s, 3H), 2.71 (s, 3H). Mass spectrum (MALDI-TOF, CHCA matrix, m/z): Calcd. for C19H13NO2S3F6, 498.0 (M+H), found 497.6.

Workup

  1. customto give
  2. customafter preparative thin-layer chromatrography purification, methyl 4-{4-[3,5-bis(trifluoromethyl)phenyl]-5-methyl(1,3-thiazol-2-yl)}-5-methylthiothiophene-2-carboxylate (16.2 mg, 11%) as a solid

Sources & evidence

ORD record
ord-451ff43cf0924528a582cdef1ad3515e
Source dataset
uspto-grants-2002_12
Patent number
US06492403B1

Reaction notes

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