3,5-Dichloro-N-[(2S)-2-(4-fluorophenyl)pent-4-en-1-yl]-N-methylbenzamide → 3-cyano-N-ethyl-N-[(2S)-2-(4-fluorophenyl)-4-oxobutyl]-5,6,7,8-tetrahydronaphthalene-1-carboxamide

HRID 749460Notes

Reaction equation

HRID 749460 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:13]([N:15]([CH2:28][CH3:29])[CH2:16][C@H:17]([C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)[CH2:18][CH:19]=C)=[O:14])[C:6]2[CH2:7][CH2:8][CH2:9][CH2:10][C:11]=2[CH:12]=1)#[N:2].ClC1C=C(C=C(Cl)C=1)C(N(C[C@H](C1C=CC(F)=CC=1)CC=C)C)=[O:35]>>[C:1]([C:3]1[CH:4]=[C:5]([C:13]([N:15]([CH2:28][CH3:29])[CH2:16][C@H:17]([C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)[CH2:18][CH:19]=[O:35])=[O:14])[C:6]2[CH2:7][CH2:8][CH2:9][CH2:10][C:11]=2[CH:12]=1)#[N:2]

Participants

3

Reactant 2

HCID 689786383,5-Dichloro-N-[(2S)-2-(4-fluorophenyl)pent-4-en-1-yl]-N-methylbenzamideHCID 689787003-cyano-N-ethyl-N-[(2S)-2-(4-fluorophenyl)pent-4-en-1-yl]-5,6,7,8-tetrahydronaphthalene-1-carboxamide

Product 1

HCID 586835293-cyano-N-ethyl-N-[(2S)-2-(4-fluorophenyl)-4-oxobutyl]-5,6,7,8-tetrahydronaphthalene-1-carboxamide

Procedure

The compound was synthesized in an analogous way to that of Method 21b but using 3-cyano-N-ethyl-N-[(2S)-2-(4-fluorophenyl)pent-4-en-1-yl]-5,6,7,8-tetrahydronaphthalene-1-carboxamide rather than 3,5-dichloro-N-[(2S)-2-(4-fluorophenyl)pent-4-en-1-yl]-N-methylbenzamide (yield, 70%). 1H NMR (500 MHz, CDCl3): 0.9-4.2 (cm, 18H), 5.9 (s, <1H), 6.9-7.5 (cm, 6H), 8.0 (s, <1H), 9.7 (m, 1H). LCMS: m/z 393 (M+1)+.

Workup

  1. customThe compound was synthesized in an analogous way to that of Method 21b

Sources & evidence

ORD record
ord-a819bf12dc954cf0997d72e034bbda1c
Source dataset
uspto-grants-2008_07
Patent number
US07402581B2

Reaction notes

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