Acetaminophen → N-[4-({(2R)-2-[5-Cyano-2-methyl-4-(trifluoromethyl)-1H-indol-1-yl]propyl}oxy)phenyl]acetamide

HRID 2102160Notes

Reaction equation

HRID 2102160 reaction equation
[OH:1][CH2:2][C@H:3]([N:5]1[C:13]2[C:8](=[C:9]([C:16]([F:19])([F:18])[F:17])[C:10]([C:14]#[N:15])=[CH:11][CH:12]=2)[CH:7]=[C:6]1[CH3:20])[CH3:4].O[C:22]1[CH:27]=[CH:26][C:25]([NH:28][C:29](=[O:31])[CH3:30])=[CH:24][CH:23]=1>>[C:14]([C:10]1[C:9]([C:16]([F:19])([F:17])[F:18])=[C:8]2[C:13](=[CH:12][CH:11]=1)[N:5]([C@H:3]([CH3:4])[CH2:2][O:1][C:22]1[CH:27]=[CH:26][C:25]([NH:28][C:29](=[O:31])[CH3:30])=[CH:24][CH:23]=1)[C:6]([CH3:20])=[CH:7]2)#[N:15]

Participants

3

Reactant 2

HCID 1983AcetaminophenHCID 674048201-[(1R)-2-Hydroxy-1-methylethyl]-2-methyl-4-(trifluoromethyl)-1H-indole-5-carbonitrile

Product 1

HCID 67405145N-[4-({(2R)-2-[5-Cyano-2-methyl-4-(trifluoromethyl)-1H-indol-1-yl]propyl}oxy)phenyl]acetamide

Procedure

Synthesized as described in Example 139C using 1-[(1R)-2-hydroxy-1-methylethyl]-2-methyl-4-(trifluoromethyl)-1H-indole-5-carbonitrile (Example 329) and N-(4-hydroxyphenyl)acetamide: 1H NMR (400 MHz, CDCl3) δ 7.55 (d, J=8.5 Hz, 1H), 7.49 (d, J=8.5 Hz, 1H), 7.25 (d, J=8.8 Hz, 2H), 7.13 (s, 1H), 6.55 (m, 3H), 4.57 (m, 1H), 4.36 (m, 1H), 4.27 (m, 1H), 2.53 (s, 3H), 2.11 (s, 3H), 1.38 (d, J=6.1 Hz, 3H); MS (ES) m/z 414 (M−1).

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-69b69c638ab74d57b50a2afcbd3fe8fd
Source dataset
uspto-grants-2009_08
Patent number
US07572820B2

Reaction notes

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