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

HRID 749482Notes

Reaction equation

HRID 749482 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:12]([N:14]([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)[CH3:15])=[O:13])[C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:10]=2[CH:11]=1.FC1C=CC([C@H](CC=C)CN(C)C(=[O:53])C2C=C(C(F)(F)F)C=C(C(F)(F)F)C=2)=CC=1>>[F:1][C:2]1[CH:3]=[C:4]([C:12]([N:14]([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:53])[CH3:15])=[O:13])[C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:10]=2[CH:11]=1

Participants

3

Reactant 2

HCID 689786443-fluoro-N-[(2S)-2-(4-fluorophenyl)pent-4-en-1-yl]-N-methyl-5,6,7,8-tetrahydronaphthalene-1-carboxamideHCID 86606886N-[(2S)-2-(4-fluorophenyl)pent-4-en-1-yl]-N-methyl-3,5-bis(trifluoromethyl)benzamide

Product 1

HCID 112456923-fluoro-N-[(2S)-2-(4-fluorophenyl)-4-oxobutyl]-N-methyl-5,6,7,8-tetrahydronaphthalene-1-carboxamide

Procedure

The compound was synthesized in an analogous way to that of Method 20b but using 3-fluoro-N-[(2S)-2-(4-fluorophenyl)pent-4-en-1-yl]-N-methyl-5,6,7,8-tetrahydronaphthalene-1-carboxamide rather than N-[(2S)-2-(4-fluorophenyl)pent-4-en-1-yl]-N-methyl-3,5-bis(trifluoromethyl)benzamide (yield, 68%). 1H NMR (500 MHz, CDCl3): 1.6-4.2 (cm, 16H), 6.2-7.8 (cm, 6H), 9.8 (s, 1H).

Workup

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

Sources & evidence

ORD record
ord-0d360113f99e4d099bbb1aa82647deb5
Source dataset
uspto-grants-2008_07
Patent number
US07402581B2

Reaction notes

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