2-Amino-5-methylthiazole → 2,2-Dimethyl-trans-N-(5-methylthiazol-2-yl)-3-phenylcyclopropanecarboxamide

HRID 2174602Notes

Reaction equation

HRID 2174602 reaction equation
[CH3:1][C:2]1([CH3:14])[C@@H:4]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[C@@H:3]1[C:11]([OH:13])=O.[NH2:15][C:16]1[S:17][C:18]([CH3:21])=[CH:19][N:20]=1>>[CH3:14][C:2]1([CH3:1])[C@@H:4]([C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=2)[C@@H:3]1[C:11]([NH:15][C:16]1[S:17][C:18]([CH3:21])=[CH:19][N:20]=1)=[O:13]

Participants

3

Reactant 2

HCID 3517702-Amino-5-methylthiazoleHCID 68582304(1S,3S)-2,2-dimethyl-3-phenylcyclopropane-1-carboxylic acid

Product 1

HCID 867097352,2-Dimethyl-trans-N-(5-methylthiazol-2-yl)-3-phenylcyclopropanecarboxamideYield 61.8%

Procedure

2,2-Dimethyl-trans-3-phenylcyclopropanecarboxylic acid (250 mg, 1.32 mmol) and 2-amino-5-methylthiazole (150 mg, 1.31 mmol) were reacted as described under General Procedure D to furnish the title compound (232 mg, 61%) as a yellow foam. 1H NMR (300 MHz, CDCl3) δ 7.33-7.17 (m, 6H), 7.02 (s, 1H), 2.95 (d, J=5.6 Hz, 1H), 2.37 (s, 3H), 2.08 (d, J=5.6 Hz, 1H), 1.44 (s, 3H), 1.03 (s, 3H). mp 132-135° C. ESIMS m/z [M+H]+ 287.1.

Sources & evidence

ORD record
ord-7906e673329049f7873cbb5cbcf3592c
Source dataset
uspto-grants-2015_06
Patent number
US09062013B2

Reaction notes

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