4-cyclohexylphenylthiourea → HCID 86583848, compound

HRID 2298662Notes

Reaction equation

[Br:1][CH2:2][C:3]([C:5]1[CH:6]=[C:7]([C:11]([O:13][CH3:14])=[S:12])[S:8][C:9]=1[CH3:10])=O.[CH:15]1([C:21]2[CH:26]=[CH:25][C:24]([NH:27][C:28]([NH2:30])=[S:29])=[CH:23][CH:22]=2)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1>>[BrH:1].[CH:15]1([C:21]2[CH:22]=[CH:23][C:24]([NH:27][C:28]3[S:29][CH:2]=[C:3]([C:5]4[CH:6]=[C:7]([C:11]([O:13][CH3:14])=[S:12])[S:8][C:9]=4[CH3:10])[N:30]=3)=[CH:25][CH:26]=2)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]1

Participants

Reactant 2

HCID 27321804-cyclohexylphenylthiourea

HCID 86583828Methyl 4-(2-bromoacetyl)-5-methylthiothiophene-2-carboxylate

Product 1

HCID 86583848HCID 86583848, compoundYield 42.1%

Procedure

Methyl 4-(2-bromoacetyl)-5-methylthiothiophene-2-carboxylate (65 mg, 0.21 mmol) was allowed to react with 4-cyclohexylphenylthiourea (49.2 mg) as described in Example 154, step (a) to give 45 mg (41% yield) of methyl 4-{2-[(4-cyclohexylphenyl)amino](1,3-thiazol-4-yl)}-5-methylthiothiophene-2-carboxylate hydrobromide. 1H NMR (DMSO-d6, 300 MHz) δ1.23-1.39 (m, 5H), 1.71-1.79 (m, 5H), 2.68 (s, 3H), 3.83 (s, 3H), 7.16 (d, 2H, J=8.6 Hz), 7.26 (s, 1H), 7.65 (d, 2H, J=8.7 Hz), 8.14 (s, 1H), 10.19 (s, 1H); Mass Spectrum (ESI) m/z calcd. for C22H24N2O2S3, 444.64 (M+H), found 445.2.

Sources & evidence

ORD record: ord-51376fdc168344228f54362868434cf3
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06492403B1

Reaction notes

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