(2-Fluorophenyl)thiourea → HCID 86758181, compound

HRID 2186616Notes

Reaction equation

HRID 2186616 reaction equation
Br.[F:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][C:10]1[S:11][CH:12]=[C:13]([C:15]2[C:19](=[CH2:20])[S:18][CH:17]([C:21]([O:23][CH3:24])=[S:22])[CH:16]=2)[N:14]=1.[Br:25]CC(C1C=C(C(OC)=S)SC=1C)=O.FC1C=CC=CC=1NC(N)=S>>[BrH:25].[F:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][C:10]1[S:11][CH:12]=[C:13]([C:15]2[CH:16]=[C:17]([C:21]([O:23][CH3:24])=[S:22])[S:18][C:19]=2[CH3:20])[N:14]=1

Participants

4

Reactant 3

HCID 2737500(2-Fluorophenyl)thioureaHCID 86583828Methyl 4-(2-bromoacetyl)-5-methylthiothiophene-2-carboxylateHCID 131723298HCID 131723298, compound

Product 1

HCID 86758181HCID 86758181, compoundYield 70%

Procedure

Methyl 4-{2-[(2-fluorophenyl)amino](1,3-thiazol-4-yl)}-5-methlylthiothiophene-2-carboxylate hydrobromide: Methyl 4-(2-bromoacetyl)-5-methylthiothiophene-2-carboxylate (60 mg, 0.19 mmol) was allowed to react with 2-fluorophenyl thiourea as described in Example 154, step (a) to give 55.6 mg (70% yield) of methyl 4-{2-[(2-fluorophenyl)amino](1,3-thiazol-4-yl)}-5-methylthiothiophene-2-carboxylate hydrobromide. 1H NMR (DMSO-d6, 300 MHz) δ 2.68 (s, 3H), 3.83 (s, 3H), 6.96-7.04 (m, 1H), 7.14-7.29 (m, 3H), 7.35 (s, 1H), 8.06, 8.14 (s, 1H rotomer), 8.61 (td, 1H rotomer, J=1.5, 8.5 Hz), 10.14, 10.30 (s, 1H rotomer); Mass Spectrum (ESI) m/z calcd. for C16H13FN2O2S3, 380.48 (M+H), found 381.1.

Sources & evidence

ORD record
ord-a909ae4401434ce19d298c25135af179
Source dataset
uspto-grants-2002_06
Patent number
US06403633B2

Reaction notes

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