1-[2-(4-Amino-2-chlorophenyl)ethyl]4-trifluoromethylpiperidin-4-ol → 3-(3-Bromobiphenyl-4-yl)propynoic acid-{3-chloro-4-[2-(4-hydroxy-4-trifluoromethylpiperidin-1-yl)ethyl]phenyl}amide

HRID 735162Notes

Reaction equation

HRID 735162 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:5]=[CH:6][C:7]=1[C:8]#[C:9][C:10]([OH:12])=O.[NH2:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][N:28]2[CH2:33][CH2:32][C:31]([C:35]([F:38])([F:37])[F:36])([OH:34])[CH2:30][CH2:29]2)=[C:22]([Cl:39])[CH:21]=1>>[Cl:39][C:22]1[CH:21]=[C:20]([NH:19][C:10](=[O:12])[C:9]#[C:8][C:7]2[CH:6]=[CH:5][C:4]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:3][C:2]=2[Br:1])[CH:25]=[CH:24][C:23]=1[CH2:26][CH2:27][N:28]1[CH2:33][CH2:32][C:31]([OH:34])([C:35]([F:37])([F:38])[F:36])[CH2:30][CH2:29]1

Participants

3

Reactant 2

HCID 688160431-[2-(4-Amino-2-chlorophenyl)ethyl]4-trifluoromethylpiperidin-4-olHCID 68818231(3-bromobiphenyl-4-yl)propynoic Acid

Product 1

HCID 578457473-(3-Bromobiphenyl-4-yl)propynoic acid-{3-chloro-4-[2-(4-hydroxy-4-trifluoromethylpiperidin-1-yl)ethyl]phenyl}amide

Procedure

Prepared analogously to Example 2.3.f. from (3-bromobiphenyl-4-yl)propynoic acid and 1-[2-(4-amino-2-chlorophenyl)ethyl]4-trifluoromethylpiperidin-4-ol. Yield: 36 mg (10.5% of theory); C29H25BrClF3N2O2 (M=605.87); calc.: molecular ion peak (M+H)+: 605/07/09; found: molecular ion peak (M+H)+: 605/07/09.

Workup

  1. customPrepared analogously to Example 2.3.f

Sources & evidence

ORD record
ord-615db3aa2ba54a78aa58746b84119504
Source dataset
uspto-grants-2009_09
Patent number
US07592373B2

Reaction notes

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