Potassium Carbonate → 2-(2-(3-((4-(2-Hydroxyethyl)piperidin-1-yl)methyl)benzamido)-5-(piperidin-1-yl)phenyl)-N-(3-(trifluoromethyl)benzyl)isonicotinamide

HRID 1408013Notes

Reaction equation

HRID 1408013 reaction equation
Cl[CH2:2][C:3]1[CH:4]=[C:5]([CH:41]=[CH:42][CH:43]=1)[C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)=[CH:11][C:10]=1[C:21]1[CH:22]=[C:23]([CH:38]=[CH:39][N:40]=1)[C:24]([NH:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([C:34]([F:37])([F:36])[F:35])[CH:29]=1)=[O:25])=[O:7].[NH:44]1[CH2:49][CH2:48][CH:47]([CH2:50][CH2:51][OH:52])[CH2:46][CH2:45]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[OH:52][CH2:51][CH2:50][CH:47]1[CH2:48][CH2:49][N:44]([CH2:2][C:3]2[CH:4]=[C:5]([CH:41]=[CH:42][CH:43]=2)[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([N:15]3[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]3)=[CH:11][C:10]=2[C:21]2[CH:22]=[C:23]([CH:38]=[CH:39][N:40]=2)[C:24]([NH:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([C:34]([F:37])([F:36])[F:35])[CH:29]=2)=[O:25])=[O:7])[CH2:45][CH2:46]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 739534-PiperidineethanolHCID 665867362-(2-(3-(chloromethyl)benzamido)-5-(piperidin-1-yl)phenyl)-N-(3-(trifluoromethyl)benzyl)-isonicotinamide

Product 1

HCID 665880842-(2-(3-((4-(2-Hydroxyethyl)piperidin-1-yl)methyl)benzamido)-5-(piperidin-1-yl)phenyl)-N-(3-(trifluoromethyl)benzyl)isonicotinamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 20 mg of 2-(2-(3-(chloromethyl)benzamido)-5-(piperidin-1-yl)phenyl)-N-(3-(trifluoromethyl)benzyl)isonicotinamide 8.1a, 5.2 mg of 2-(piperidin-4-yl)ethanol, and 9.1 mg of K2CO3 in 2 mL of DMF was stirred for 12 h. The product was isolated by reverse phase chromatography eluting with 0.05% TFA in a water/acetonitrile gradient. MS (ES, m/z) 700.27 [M+H]+.

Workup

  1. customThe product was isolated by reverse phase chromatography
  2. washeluting with 0.05% TFA in a water/acetonitrile gradient

Sources & evidence

ORD record
ord-77db1eafd4ce4721b4abd6521cc0eaf4
Source dataset
uspto-grants-2014_12
Patent number
US08916569B2

Reaction notes

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