2-(3,5-Bis(trifluoromethyl)phenyl)propanoic acid → (RS)-alpha-Methyl-N-[1-(2-Fluorophenyl)-4-oxocyclohexyl]-3,5-bis(trifluoromethyl)benzeneacetamide

HRID 2213059Notes

Reaction equation

HRID 2213059 reaction equation
[CH3:1][CH:2]([C:6]1[CH:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:9]=[C:8]([C:16]([F:19])([F:18])[F:17])[CH:7]=1)[C:3](O)=[O:4].Cl.[F:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[C:28]1([NH2:35])[CH2:33][CH2:32][C:31](=[O:34])[CH2:30][CH2:29]1>>[CH3:1][CH:2]([C:6]1[CH:11]=[C:10]([C:12]([F:13])([F:15])[F:14])[CH:9]=[C:8]([C:16]([F:17])([F:18])[F:19])[CH:7]=1)[C:3]([NH:35][C:28]1([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2[F:21])[CH2:29][CH2:30][C:31](=[O:34])[CH2:32][CH2:33]1)=[O:4]

Participants

3

Reactant 2

HCID 115220582-(3,5-Bis(trifluoromethyl)phenyl)propanoic acidHCID 695590591-(2-Fluorophenyl)-4-oxocyclohexylamine hydrochloride

Product 1

HCID 21955300(RS)-alpha-Methyl-N-[1-(2-Fluorophenyl)-4-oxocyclohexyl]-3,5-bis(trifluoromethyl)benzeneacetamide

Procedure

Prepared from (RS)-α-methyl-3,5-bis(trifluoromethyl)benzeneacetic acid (Description 4) and 1-(2-fluorophenyl)-4-oxocyclohexylamine hydrochloride (Description 180) according to the method of Example 1. 1H NMR (360 MHz, CDCl3) δ 7.79 (1H, s), 7.68 (2H, s), 7.40–7.35 (1H, m), 7.27–7.21 (1H, m), 7.14–7.10 (1H, m), 6.93–6.86 (1H, m), 5.95 (1H, s), 3.71 (1H, q J 7.0 Hz), 3.08–3.00 (1H, m), 2.86–2.78 (1H, m), 2.56–2.20 (6H, m), and 1.49 (3H, d, J 7.0 Hz).

Sources & evidence

ORD record
ord-92d736e8e54140fdb206730bc3ad7deb
Source dataset
uspto-grants-2006_09
Patent number
US07105507B2

Reaction notes

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