4-(Trifluoromethyl)benzaldehyde → HCID 67186569, compound

HRID 735941Notes

Reaction equation

[CH2:1]([C:9]1[N:13]=[C:12]([CH2:14][CH2:15][C:16]2[CH:23]=[CH:22][C:19]([CH2:20][NH2:21])=[CH:18][CH:17]=2)[O:11][N:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[F:24][C:25]([F:35])([F:34])[C:26]1[CH:33]=[CH:32][C:29]([CH:30]=O)=[CH:28][CH:27]=1>>[CH2:1]([C:9]1[N:13]=[C:12]([CH2:14][CH2:15][C:16]2[CH:23]=[CH:22][C:19]([CH2:20][NH:21][CH2:30][C:29]3[CH:28]=[CH:27][C:26]([C:25]([F:24])([F:34])[F:35])=[CH:33][CH:32]=3)=[CH:18][CH:17]=2)[O:11][N:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

Reactant 2

HCID 679964-(Trifluoromethyl)benzaldehyde

HCID 67187005HCID 67187005, compound

Product 1

HCID 67186569HCID 67186569, compoundYield 65%

Procedure

The same procedure as employed in the preparation of Example 226 (step a) but using 4-[2-(3-octyl-1,2,4-oxadiazol-5-yl)ethyl]benzylamine and 4-(trifluoromethyl)benzaldehyde gave the title compound as a pale yellow oil (65%). 1H NMR (CDCl3, 300 MHz) δ 7.60 (d, 2H, J=8.3 Hz), 7.51 (d, 2H, J=8.3 Hz), 7.30 (d, 2H, J=7.9 Hz), 7.18 (d, 2H, J=7.9 Hz), 3.86 (s, 2H), 3.78 (s, 2H), 3.12 (m, 4H), 2.70 (t, 2H, J=7.7 Hz), 1.73 (m, 2H), 1.28 (m, 10H), 0.88 (t, 3H, J=6.6 Hz). M+(LC/MS(ESI)): 474. HPLC (Condition A), Rt: 4.31 min (HPLC purity: 97.9%).

Workup

customThe same procedure as employed in the preparation of Example 226 (step a) but

Sources & evidence

ORD record: ord-0be9e9e2549347c2a343e5de0a7db9ad
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07592477B2

Reaction notes

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