Tetrahydrofuran → HCID 86661297, compound

HRID 1685034Notes

Reaction equation

HRID 1685034 reaction equation
[NH2:1][C:2]1[S:3][C:4]([CH:10]([CH3:12])[CH3:11])=[C:5]([C:7]([O-:9])=[O:8])[N:6]=1.[F:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][N:21]=[C:22]=[O:23])[CH:15]=1.[CH2:24]1COCC1>>[F:13][C:14]1[CH:15]=[C:16]([CH:17]=[CH:18][CH:19]=1)[CH2:20][NH:21][C:22](=[O:23])[NH:1][C:2]1[S:3][C:4]([CH:10]([CH3:12])[CH3:11])=[C:5]([C:7]([O:9][CH3:24])=[O:8])[N:6]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 6434993-Fluorobenzyl isocyanateHCID 86661298HCID 86661298, compound

Product 1

HCID 86661297HCID 86661297, compound

Procedure

A THF (5 mL) solution of methy; 2-amino-5-isopropylthiazole-4-carboxylate (commercially available, 200 mg, 1 mmol) and 1-fluoro-3-(isocyanatomethyl)benzene (140 μL, 1.1 mmol) was microwave irradiated at 160 C for 35 minutes. Usual work-up concluded with recrystallization from MeOH afforded methyl 2-(3-(3-fluorobenzyl)ureido)-5-isopropylthiazole-4-carboxylate. 1H NMR (400 MHz, DMSO-d6): δ7.35 (m, 1H), 7.08 (m, 3H), 4.34 (d, 2H), 3.94 (m, 1H), 3.76 (s, 3H), 1.24 (d, 6H). MS (ES+): M/Z 452 (M+H)+.

Workup

  1. customUsual work-up concluded with recrystallization from MeOH

Sources & evidence

ORD record
ord-c4032738ebb94d97a2bb33dfcfb69235
Source dataset
uspto-grants-2012_04
Patent number
US08148380B2

Reaction notes

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