4-(2-{[4-(Dimethylamino)phenyl]amino}(1,3-thiazol-4-yl))-5-methylthiothiophene-2-carboxamidine hydrochloride → 4-{2-[(4-Methoxyphenyl)amino](1,3-thiazol-4-yl)}-5-methylthiothiophene-2-carboxamidine hydrochloride

HRID 412971Notes

Reaction equation

HRID 412971 reaction equation
[ClH:1].CN(C)[C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]2[S:12][CH:13]=[C:14]([C:16]3[CH:17]=[C:18]([C:23]([NH2:25])=[NH:24])[S:19][C:20]=3[S:21][CH3:22])[N:15]=2)=[CH:6][CH:5]=1.Br.CN(C)C1C=CC(NC2SC=C(C3([C:48]([OH:50])=S)CC=C(C)S3)N=2)=CC=1>>[ClH:1].[CH3:48][O:50][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]2[S:12][CH:13]=[C:14]([C:16]3[CH:17]=[C:18]([C:23]([NH2:25])=[NH:24])[S:19][C:20]=3[S:21][CH3:22])[N:15]=2)=[CH:6][CH:5]=1

Participants

3

Reactant 2

HCID 185370624-(2-{[4-(Dimethylamino)phenyl]amino}(1,3-thiazol-4-yl))-5-methylthiothiophene-2-carboxamidine hydrochlorideHCID 178419508HCID 178419508, compound

Product 1

HCID 185368664-{2-[(4-Methoxyphenyl)amino](1,3-thiazol-4-yl)}-5-methylthiothiophene-2-carboxamidine hydrochlorideYield 22%

Procedure

4-(2-{[4-(Dimethylamino)phenyl]amino}(1,3-thiazol-4-yl))-5-methylthiothiophene-2-carboxamidine hydrochloride: Methyl 4-(2-{([4-(dimethylamino)phenyl]amino}(1,3-thiazol-4-yl))-5-methylthiothiophene-2-carboxylate hydrobromide (50 mg, 0.10 mmol) was treated as described in Example 154, step (b) to give 9.4 mg (22% yield) of 4-{2-[(4-methoxyphenyl)amino](1,3-thiazol-4-yl)}-5-methylthiothiophene-2-carboxamidine hydrochloride. 1H NMR (DMSO-d6, 300 MHz) 2.70 (s, 3H), 2.84 (s, 6H), 6.75 (d, 2H, J=9.2 Hz), 7.00 (s, 1H), 7.56 (d, 2H, J=9.1 Hz), 8.31 (s, 1H), 8.68 (bs, 3H), 9.92 (bs, 1H).

Sources & evidence

ORD record
ord-728b0efbca2741f6a7196fc140450ce8
Source dataset
uspto-grants-2003_05
Patent number
US06562840B1

Reaction notes

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