Cyclopentyl 4-trifluoromethylphenyl ketone → N-{cyclopentyl[4-(trifluoromethyl)phenyl]methyl}-N-[4-(3-undecyl-1,2,4-oxadiazol-5-yl)benzyl]amine

HRID 735895Notes

Reaction equation

[CH:1]1([C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=2)=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:18]([C:29]1[N:33]=[C:32]([C:34]2[CH:41]=[CH:40][C:37]([CH2:38][NH2:39])=[CH:36][CH:35]=2)[O:31][N:30]=1)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]>>[CH:1]1([CH:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=2)[NH:39][CH2:38][C:37]2[CH:36]=[CH:35][C:34]([C:32]3[O:31][N:30]=[C:29]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[N:33]=3)=[CH:41][CH:40]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

Reactant 2

HCID 24724174Cyclopentyl 4-trifluoromethylphenyl ketone

HCID 67187547HCID 67187547, compound

Product 1

HCID 67187255N-{cyclopentyl[4-(trifluoromethyl)phenyl]methyl}-N-[4-(3-undecyl-1,2,4-oxadiazol-5-yl)benzyl]amineYield 55%

Procedure

The same procedure as employed in the preparation of Example 223 (step b) but using cyclopentyl[4-(trifluoromethyl)phenyl]methanone and 4-(3-undecyl-1,2,4-oxadiazol-5-yl)benzylamine gave the title compound as a colorless oil (55%). 1H NMR (DMSO-d6, 300 MHz) δ 8.00 (d, 2H), 7.64 (m, 2H), 7.50 (m, 4H), 3.62-3.34 (m, 2H), 2.74 (m, 2H), 2.12-1.85 (m, 2H), 1.70 (m, 2H), 1.60-0.92 (m, 25H), 0.83 (m, 3H). HPLC (Condition A), Rt: 5.42 min (HPLC purity: 98.3%).

Workup

customThe same procedure as employed in the preparation of Example 223 (step b)

Sources & evidence

ORD record: ord-91986d5eeee14f3b89cc3196d709d02a
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07592477B2

Reaction notes

Loading…