HCID 86583844, compound → HCID 18537450, compound

HRID 1058475Notes

Reaction equation

[ClH:1].[Cl:2]C1C=CC(OC2C=CC(NC3SC=C([C:20]4([C:27]([NH2:29])=[NH:28])[CH2:24][CH:23]=[C:22]([S:25][CH3:26])[S:21]4)N=3)=CC=2)=CC=1.Br.Cl[C:34]1[CH:62]=[CH:61][C:37]([O:38][C:39]2[CH:44]=[CH:43][C:42]([NH:45][C:46]3[S:47][CH:48]=[C:49](C4C=C(C(OC)=S)SC=4C)[N:50]=3)=[CH:41][CH:40]=2)=[CH:36][CH:35]=1>>[ClH:2].[Cl:1][C:34]1[CH:62]=[CH:61][C:37]([O:38][C:39]2[CH:40]=[CH:41][C:42]([NH:45][C:46]3[S:47][CH:48]=[C:49]([C:23]4[CH:24]=[C:20]([C:27]([NH2:29])=[NH:28])[S:21][C:22]=4[S:25][CH3:26])[N:50]=3)=[CH:43][CH:44]=2)=[CH:36][CH:35]=1

Participants

Reactant 2

HCID 86583844HCID 86583844, compound

HCID 86758827HCID 86758827, compound

Product 1

HCID 18537450HCID 18537450, compoundYield 49%

Procedure

4-(2-{[4-(4-Chlorophenoxy)phenyl]amino(1,3-thiazol-4-yl)}-5-methylthiothiophene-2-carboxamidine hydrochloride: Methyl 4-(2-{[4-(4-chlorophenoxy)phenyl]amino}(1,3-thiazol-4-yl))-5-methylthiothiophene-2-carboxylate hydrobromide (300 mg, 0.52 mmol) was treated as described in Example 154, step (b) to give 129.9 mg (49% yield) of 4-(2-{[4-(4-chlorophenoxy)phenyl]amino}(1,3-thiazol-4-yl))-5-methylthiothiophene-2-carboxamidine hydrochloride. 1H NMR (DMSO-d6, 300 MHz) δ 2.72 (s, 3H), 6.97 (m, 2H), 7.07 (m, 2H), 7.15 (s, 1H), 7.40 (m, 2H), 7.85 (m, 2H), 8.46 (s, 1H), 8.82 (bs, 2H), 9.27 (bs, 2H), 10.43 (bss, 1H); Mass Spectrum (ESI) m/z calcd. for C21H17ClN4OS3, 473.1 (M+H), found 473.2, 475.1.

Sources & evidence

ORD record: ord-6c63204955464bd7a37c83a28823a695
Source dataset: uspto-grants-2003_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06515002B2

Reaction notes

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