N-(3,4,5-Trimethoxyphenyl)thiourea → Isopropyl 5-methyl-4-{2-[(3,4,5-trimethoxyphenyl)amino](1,3-thiazol-4-yl)}thiophene-2-carboxylate hydrobromide

HRID 2298665Notes

Reaction equation

HRID 2298665 reaction equation
[CH:1]([O:4][C:5]([C:7]1[S:8][C:9]([CH3:16])=[C:10]([C:12](=O)[CH2:13][Br:14])[CH:11]=1)=[O:6])([CH3:3])[CH3:2].[CH3:17][O:18][C:19]1[CH:20]=[C:21]([NH:29][C:30]([NH2:32])=[S:31])[CH:22]=[C:23]([O:27][CH3:28])[C:24]=1[O:25][CH3:26]>>[BrH:14].[CH3:16][C:9]1[S:8][C:7]([C:5]([O:4][CH:1]([CH3:3])[CH3:2])=[O:6])=[CH:11][C:10]=1[C:12]1[N:32]=[C:30]([NH:29][C:21]2[CH:22]=[C:23]([O:27][CH3:28])[C:24]([O:25][CH3:26])=[C:19]([O:18][CH3:17])[CH:20]=2)[S:31][CH:13]=1

Participants

3

Reactant 2

HCID 2760811N-(3,4,5-Trimethoxyphenyl)thioureaHCID 18537306Isopropyl 4-(2-bromoacetyl)-5-methylthiophene-2-carboxylate

Product 1

HCID 18536836Isopropyl 5-methyl-4-{2-[(3,4,5-trimethoxyphenyl)amino](1,3-thiazol-4-yl)}thiophene-2-carboxylate hydrobromideYield 48%

Procedure

Isopropyl-4-(2-bromoacetyl)-5-methylthiophene-2-carboxylate (84 mg, 0.27 mmol) was allowed to react with 3,4,5-trimethoxyphenylthiourea (66.5 mg) as described in Example 154, step (a) to give 68 mg (48% yield) of isopropyl 5-methyl-4-{2-[(3,4,5-trimethoxyphenyl)amino](1,3-thiazol-4-yl)}thiophene-2-carboxylate hydrobromide. Mass Spectrum (ESI) m/z calcd. For C21H24N2O5S2, 448.56 (M+H), found 449.0.

Sources & evidence

ORD record
ord-69c41590839648fd9cca6f6727d16429
Source dataset
uspto-grants-2002_12
Patent number
US06492403B1

Reaction notes

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