HCID 86583848, compound → HCID 18537254, compound

HRID 412974Notes

Reaction equation

HRID 412974 reaction equation
[ClH:1].C1(C2C=CC([C:14]3[S:15][C:16](N)=[C:17]([C:19]4[CH:20]=[C:21]([C:26]([NH2:28])=[NH:27])[S:22][C:23]=4[S:24][CH3:25])[N:18]=3)=CC=2)CCCCC1.Br.[CH:31]1([C:37]2[CH:42]=[CH:41][C:40]([NH:43]C3SC=C(C4C=C(C(OC)=S)SC=4C)N=3)=[CH:39][CH:38]=2)[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1>>[ClH:1].[CH:31]1([C:37]2[CH:38]=[CH:39][C:40]([NH:43][C:14]3[S:15][CH:16]=[C:17]([C:19]4[CH:20]=[C:21]([C:26]([NH2:28])=[NH:27])[S:22][C:23]=4[S:24][CH3:25])[N:18]=3)=[CH:41][CH:42]=2)[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36]1

Participants

3

Reactant 2

HCID 86583848HCID 86583848, compoundHCID 86758976HCID 86758976, compound

Product 1

HCID 18537254HCID 18537254, compoundYield 47%

Procedure

4-{2-(4-Cyclohexylphenyl)amino(1,3-thiazol-4-yl)}-5-methylthiothiophene-2-carboxamidine hydrochloride: Methyl 4-{2-[(4-cyclohexylphenyl)amino](1,3-thiazol-4-yl)}-5-methylthiothiophene-2-carboxylate hydrobromide (31.1 mg, 0.059 mmol) was treated as described in Example 154, step (b) to give 12.8 mg (47% yield) of 4-{2-[(4-cyclohexylphenyl)amino](1,3-thiazol-4-yl)}-5-methylthiothiophene-2-carboxamidine hydrochloride. 1H NMR (DMSO-d6, 300 MHz) δ 1.33-1.40 (m, 5H), 1.68-1.79 (m, 5H), 2.44 (m, 1H), 2.73 (s, 3H), 7.12 (s, 1H), 7.18 (d, 2H, J=8.7 Hz), 7.68 (d, 2H, J=8.7 Hz), 8.47 (s, 1H), 8.85 (bs, 2H), 9.32 (bs, 2H), 10.28 (s, 1H); Mass Spectrum (ESI) m/z calcd. for C21H24N4S3, 428.64 (M+H), found 429.2.

Sources & evidence

ORD record
ord-6bf270b9b0d8459a9a9056cdaba04181
Source dataset
uspto-grants-2003_05
Patent number
US06562840B1

Reaction notes

Loading…