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

반응식

[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

참가 물질

반응물 3

HCID 676454Phenylthiourea

HCID 2781759Thiophene-2-carboximidamide Hydrochloride

HCID 18537295Isopropyl 5-methyl-4-[2-(phenylamino)(1,3-thiazol-4-yl)]-thiophene-2-carboxylate hydrobromide

생성물 1

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

실험 절차

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.