Potassium Carbonate → HCID 69631402, compound

HRID 625275Notes

Reaction equation

HRID 625275 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].[CH3:44][O:45][CH2:46][CH2:47][NH:48][C:49]([C@H:51]1[CH2:56][CH2:55][CH2:54][NH:53][CH2:52]1)=[O:50].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:44][O:45][CH2:46][CH2:47][NH:48][C:49]([C@H:51]1[CH2:56][CH2:55][CH2:54][N:53]([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])[CH2:52]1)=[O:50]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 28162916(S)-N-(2-methoxyethyl)piperidine-3-carboxamideHCID 665867362-(2-(3-(chloromethyl)benzamido)-5-(piperidin-1-yl)phenyl)-N-(3-(trifluoromethyl)benzyl)-isonicotinamide

Product 1

HCID 69631402HCID 69631402, compoundYield 92.2%

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, 8.8 mg of (S)—N-(2-methoxyethyl)piperidine-3-carboxamide and 13.7 mg of K2CO3 in 0.33 mL of DMF was stirred for 2 h. The product was isolate by preparative reverse phase HPLC eluting with 0.05% TFA in a water/acetonitrile gradient to give 23 mg of product. MS (ES, m/z) 757.3 [M+H]+

Workup

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

Sources & evidence

ORD record
ord-f06c407e50ad4573adbfcbe9ae7e5458
Source dataset
uspto-grants-2016_04
Patent number
US09301951B2

Reaction notes

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