(2,5-dimethoxyphenyl)thiourea → HCID 86583829, compound

HRID 2186614Notes

Reaction equation

HRID 2186614 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.[CH3:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][C:18]=1[NH:25][C:26]([NH2:28])=[S:27]>>[BrH:1].[CH3:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][C:18]=1[NH:25][C:26]1[S:27][CH:2]=[C:3]([C:5]2[CH:6]=[C:7]([C:11]([O:13][CH3:14])=[S:12])[S:8][C:9]=2[CH3:10])[N:28]=1

Participants

3

Reactant 2

HCID 2758483(2,5-dimethoxyphenyl)thioureaHCID 86583828Methyl 4-(2-bromoacetyl)-5-methylthiothiophene-2-carboxylate

Product 1

HCID 86583829HCID 86583829, compoundYield 89.6%

Procedure

Methyl 4-{2-[(2,5-dimethoxyphenyl)amino](1,3-thiazol-4-yl)}-5-tethylthiothiophene-2-carboxylate hydrobromide: Methyl 4-(2-bromoacetyl)-5-methylthiothiophene-2-carboxylate (49.4 mg, 0.15 mmol) was allowed to react with 2,5-dimethoxy phenyl thiourea (37.2 mg) as described in Example 154, step (a), to give 65.5 mg (87% yield) of methyl 4-{2-[(2,5-dimethoxyphenyl)amino](1,3-thiazol-4-yl)}-5-methylthiothiophene-2-carboxylate hydrobromide. 1H NMR (DMSO-d6, 300 MHz) δ 2.66 (s, 3H), 3.76 (s, 3H), 3.81 (s, 3H), 3.83 (s, 3H), 6.49 (dd, 1H, J=3.0, 8.8 Hz), 6.92 (d, 1 H, J=8.9 Hz), 7.26 (s, 1H), 8.17 (s, 1H), 8.37 (d, 1H, J=3.1 Hz), 9.70 (s, 1H); Mass Spectrum (ESI) m/z calcd. for C18H18N2O4S3, 422.54 (M+H), found 423.1.

Sources & evidence

ORD record
ord-9507ddb132b344f5ac43eb6977d7a8b1
Source dataset
uspto-grants-2002_06
Patent number
US06403633B2

Reaction notes

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