3-cyano-N-[(2S)-2-(4-fluorophenyl)pent-4-en-1-yl]-N-methyl-1-naphthamide → 3-Cyano-N-[(2S)-2-(4-fluorophenyl)-4-oxobutyl]-N-methyl-1-naphthamide

HRID 749461Notes

Reaction equation

HRID 749461 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:13]([N:15]([CH2:17][C@H:18]([C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)[CH2:19][CH:20]=C)[CH3:16])=[O:14])[C:6]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[CH:8][CH:7]=2)#[N:2].FC1C=CC([C@H](CC=C)CN(C)C(=[O:54])C2C=C(C(F)(F)F)C=C(C(F)(F)F)C=2)=CC=1>>[C:1]([C:3]1[CH:4]=[C:5]([C:13]([N:15]([CH2:17][C@H:18]([C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)[CH2:19][CH:20]=[O:54])[CH3:16])=[O:14])[C:6]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[CH:8][CH:7]=2)#[N:2]

Participants

3

Reactant 2

HCID 689772943-cyano-N-[(2S)-2-(4-fluorophenyl)pent-4-en-1-yl]-N-methyl-1-naphthamideHCID 86606886N-[(2S)-2-(4-fluorophenyl)pent-4-en-1-yl]-N-methyl-3,5-bis(trifluoromethyl)benzamide

Product 1

HCID 114287773-Cyano-N-[(2S)-2-(4-fluorophenyl)-4-oxobutyl]-N-methyl-1-naphthamide

Procedure

The compound was synthesized in an analogous way to that of Method 20b but using 3-cyano-N-[(2S)-2-(4-fluorophenyl)pent-4-en-1-yl]-N-methyl-1-naphthamide rather than N-[(2S)-2-(4-fluorophenyl)pent-4-en-1-yl]-N-methyl-3,5-bis(trifluoromethyl)benzamide (yield, 78%). 1H NMR (400 MHz, CDCl3): 2.4-2.6 (m, 1H), 2.7 (s, 3H), 2.8-4.4 (cm, 4H), 6.2 (s, <1H), 6.8-7.8 (cm, 9H), 8.2 (s, 1H), 9.8 (s, 1H).

Workup

  1. customThe compound was synthesized in an analogous way to that of Method 20b

Sources & evidence

ORD record
ord-66d33fdf573749f1ae2d4990f9997ad8
Source dataset
uspto-grants-2008_07
Patent number
US07402581B2

Reaction notes

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