Methyl 4-(2-bromoacetyl)-5-methylthiothiophene-2-carboxylate → Methyl 4-(2-{[4-(dimethylamino)phenyl]amino}(1,3-thiazol-4-yl))-5-methylthiothiophene-2-carboxylate hydrobromide

HRID 412970Notes

Reaction equation

HRID 412970 reaction equation
[CH3:1][N:2]([CH3:25])[C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]2[S:11][CH:12]=[C:13]([C:15]3[CH:16]=[C:17]([C:21]([O:23][CH3:24])=[S:22])[S:18][C:19]=3[CH3:20])[N:14]=2)=[CH:5][CH:4]=1.[Br:26]CC(C1C=C(C(OC)=S)SC=1C)=O>>[BrH:26].[CH3:25][N:2]([CH3:1])[C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]2[S:11][CH:12]=[C:13]([C:15]3[CH:16]=[C:17]([C:21]([O:23][CH3:24])=[S:22])[S:18][C:19]=3[CH3:20])[N:14]=2)=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 86583828Methyl 4-(2-bromoacetyl)-5-methylthiothiophene-2-carboxylateHCID 86584790Methyl 4-(2-{[4-(dimethylamino)phenyl]amino}(1,3-thiazol-4-yl))-5-methylthiothiophene-2-carboxylate

Product 1

HCID 86584789Methyl 4-(2-{[4-(dimethylamino)phenyl]amino}(1,3-thiazol-4-yl))-5-methylthiothiophene-2-carboxylate hydrobromideYield 75%

Procedure

Methyl 4-(2-{[4-(dimethylamino)phenyl]amino}(1,3-thiazol-4-yl))-5-methylthiothiophene-2-carboxylate hIydrobromide: Methyl 4-(2-bromoacetyl)-5-methylthiothiophene-2-carboxylate (50 mg, 0.16 mmol) was allowed to react with 4-N,N-dimethylaminophenyl thiourea (31.5 mg) as described in Example 154, step (a), to give 53.2 mg (75% yield) of methyl 4-(2-{[4-(dimethylamino)phenyl]amino}(1,3-thiazol-4-yl))-5-methylthiothiophene-2-carboxylate hydrobromide. 1H NMR (DMSO-d6, 300 MHz) δ 2.69 (s, 3H), 3.15 (s, 6H), 3.83 (s, 3H), 7.36 (s, 1H), 7.55 (bs, 2H), 7.88 (d, 2H, J=8.3 Hz), 8.16 (s, 1H), 10.56 (bs, 1H); Mass Spectrum (ESI) m/z calcd. for C18H19N3O2S3, 405.56 (M+H), found 406.1.

Sources & evidence

ORD record
ord-9ed26fc061014014a15c456a4e5531f2
Source dataset
uspto-grants-2003_05
Patent number
US06562840B1

Reaction notes

Loading…