4-Octylaniline → Ethyl{(4-{[(4-octylphenyl)amino]carbonyl}benzyl)[4-(trifluoromethyl)benzyl]amino}(oxo)acetate

HRID 735887Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:29])[C:5]([N:7]([CH2:19][C:20]1[CH:28]=[CH:27][C:23]([C:24](O)=[O:25])=[CH:22][CH:21]=1)[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=1)=[O:6])[CH3:2].[CH2:30]([C:38]1[CH:44]=[CH:43][C:41]([NH2:42])=[CH:40][CH:39]=1)[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37]>>[CH2:1]([O:3][C:4](=[O:29])[C:5]([N:7]([CH2:19][C:20]1[CH:21]=[CH:22][C:23]([C:24]([NH:42][C:41]2[CH:43]=[CH:44][C:38]([CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])=[CH:39][CH:40]=2)=[O:25])=[CH:27][CH:28]=1)[CH2:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]([F:16])([F:17])[F:18])=[CH:13][CH:14]=1)=[O:6])[CH3:2]

Participants

Reactant 2

HCID 853464-Octylaniline

HCID 67187953HCID 67187953, compound

Product 1

HCID 68998798Ethyl{(4-{[(4-octylphenyl)amino]carbonyl}benzyl)[4-(trifluoromethyl)benzyl]amino}(oxo)acetateYield 22%

Procedure

The same procedure as employed in the preparation of Example 10 (step a) but using 4-({[ethoxy(oxo)acetyl][4-(trifluoromethyl)benzyl]amino}methyl)benzoic acid and 4-octylaniline gave the title compound as a colorless oil (22%). 1H NMR (CDCl3, 300 MHz) δ 7.89-6.60 (m, 12H), 4.48 (s, 2H), 4.44-4.21 (m, 4H), 2.65-2.36 (m, 2H), 1.68-1.40 (m, 3H), 1.38-1.08 (m, 13H), 0.81 (t, J=6.9 Hz, 3H). M+(LC/MS(ESI)): 597.7. HPLC (Condition A), Rt: 6.75 min (HPLC purity: 98.9%).

Workup

customThe same procedure as employed in the preparation of Example 10 (step a) but

Sources & evidence

ORD record: ord-8aaf29c45f884d98bd7650c17dba05d2
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07592477B2

Reaction notes

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