(1S,3S)-2,2-dimethyl-3-phenylcyclopropane-1-carboxylic acid → HCID 178427885, compound

HRID 2174603Notes

Reaction equation

HRID 2174603 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.[F:15][C:16]([F:24])([F:23])[C:17]1[CH:21]=[C:20]([NH2:22])[NH:19][N:18]=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:22][C:20]1[NH:19][N:18]=[C:17]([C:16]([F:24])([F:23])[F:15])[CH:21]=1)=[O:13]

Participants

3

Reactant 2

HCID 68582304(1S,3S)-2,2-dimethyl-3-phenylcyclopropane-1-carboxylic acidHCID 178507669HCID 178507669, compound

Product 1

HCID 178427885HCID 178427885, compoundYield 93%

Procedure

2,2-Dimethyl-trans-3-phenylcyclopropanecarboxylic acid (250 mg, 1.32 mmol) and 3-trifluoromethyl-1H-pyrazole-5-ylamine (198 mg, 1.31 mmol) were reacted as described under General Procedure D to furnish the title compound (392 mg, 93%) as a white solid. 1H NMR (300 MHz, CDCl3) δ 7.32-7.22 (m, 6H), 5.72-5.64 (m, 2H), 3.43 (d, J=6.1 Hz, 1H), 2.98 (d, J=6.1 Hz, 1H), 1.42 (s, 3H), 1.07 (s, 3H). mp 68-71° C. ESIMS m/z [M+H]+ 324.1.

Sources & evidence

ORD record
ord-66a561cb95264abeb3f4c69e512708f8
Source dataset
uspto-grants-2015_06
Patent number
US09062013B2

Reaction notes

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