Phenylthiourea → 5-Methyl-4-[2-(phenylamino)(1,3-thiazol-4-yl)]thiophene-2-carboxamidine hydrochloride

HRID 1597111Notes

Reaction equation

HRID 1597111 reaction equation
[ClH:1].[S:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:7]([NH2:9])=[NH:8].Br.CC1SC(C(OC(C)C)=O)=CC=1[C:23]1[N:24]=[C:25]([NH:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[S:26][CH:27]=1.[C:35]1(NC(N)=S)C=CC=CC=1>>[ClH:1].[CH3:35][C:6]1[S:2][C:3]([C:7]([NH2:9])=[NH:8])=[CH:4][C:5]=1[C:23]1[N:24]=[C:25]([NH:28][C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[S:26][CH:27]=1

Participants

4

Reactant 3

HCID 676454PhenylthioureaHCID 2781759Thiophene-2-carboximidamide HydrochlorideHCID 18537295Isopropyl 5-methyl-4-[2-(phenylamino)(1,3-thiazol-4-yl)]-thiophene-2-carboxylate hydrobromide

Product 1

HCID 185368965-Methyl-4-[2-(phenylamino)(1,3-thiazol-4-yl)]thiophene-2-carboxamidine hydrochlorideYield 28%

Procedure

5-Methyl-4-[2-phenylamino)(1,3-thiazol-4-yl)]thiophene-2-carboxamidine hydrochloride: Isopropyl 5-methyl-4-[2-(phenylamino)(1,3-thiazol-4-yl)]-thiophene-2-carboxylate hydrobromide (74 mg, 0.16 mmol) was treated with phenylthiourea (24.3 mg) as described in Example 154, step (b) to give 15 mg (28% yield) (of 5-methyl-4-[2-(phenylamino)(1,3-thiazol-4-yl)]thiophene-2-carboxamidine hydrochloride, which was further purified by recrystallization from methanol-water. 1H NMR (DMSO-d6, 300 MHz) δ 2.79 (s, 3H), 6.96 (t, 1H, J=7.2 Hz), 7.09 (s, 1H), 7.33 (t, 2H, J=7.5 Hz), 7.71 (d, 2H, J=7.7 Hz), 8.39 (s, 1H), 8.95 (bs, 2H), 9.33 (bs, 2H), 10.37 (s, 1H); Mass Spectrum (ESI) m/z calcd. for C15H14N4S3, 314.4 (M+H), found 315.2.

Sources & evidence

ORD record
ord-48d56c2589e54b9c9e822114c5016b76
Source dataset
uspto-grants-2001_09
Patent number
US06291514B1

Reaction notes

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