Dimethyl Sulfoxide → Tert-butyl 3-((3-((4-(piperidin-1-yl)-2-(4-(3-(trifluoromethyl)benzoyl)-pyridin-2-yl)phenyl)carbamoyl)benzyl)thio)propanoate

HRID 625265Notes

Reaction equation

HRID 625265 reaction equation
[OH:1][CH:2]([C:41]1[CH:46]=[CH:45][CH:44]=[C:43]([C:47]([F:50])([F:49])[F:48])[CH:42]=1)[C:3]1[CH:8]=[CH:7][N:6]=[C:5]([C:9]2[CH:14]=[C:13]([N:15]3[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]3)[CH:12]=[CH:11][C:10]=2[NH:21][C:22]([C:24]2[CH:25]=[C:26]([CH:38]=[CH:39][CH:40]=2)[CH2:27][S:28][CH2:29][CH2:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])=[O:23])[CH:4]=1.C(N(C(C)C)CC)(C)C.CS(C)=O>ClCCl>[N:15]1([C:13]2[CH:12]=[CH:11][C:10]([NH:21][C:22]([C:24]3[CH:25]=[C:26]([CH:38]=[CH:39][CH:40]=3)[CH2:27][S:28][CH2:29][CH2:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])=[O:23])=[C:9]([C:5]3[CH:4]=[C:3]([C:2](=[O:1])[C:41]4[CH:46]=[CH:45][CH:44]=[C:43]([C:47]([F:50])([F:48])[F:49])[CH:42]=4)[CH:8]=[CH:7][N:6]=3)[CH:14]=2)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 81531DiisopropylethylamineHCID 86705941Tert-butyl 3-((3-((2-(4-(hydroxy(3-(trifluoromethyl)phenyl)methyl)-pyridin-2-yl)-4-(piperidin-1-yl)phenyl)carbamoyl)benzyl)thio)propanoate

Product 1

HCID 66588042Tert-butyl 3-((3-((4-(piperidin-1-yl)-2-(4-(3-(trifluoromethyl)benzoyl)-pyridin-2-yl)phenyl)carbamoyl)benzyl)thio)propanoateYield 41.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A −10° C. solution of 23 mg of tert-butyl 3-((3-((2-(4-(hydroxy(3-(trifluoromethyl)phenyl)methyl)pyridin-2-yl)-4-(piperidin-1-yl)phenyl)carbamoyl)benzyl)thio)propanoate 5.2d, 17 mg of diisopropylethylamine, and 10 mg of DMSO in 0.4 mL of dichloromethane was treated with 10 mg of pyridine sulfur trioxide complex. After stirring for 1 h the reaction mixture was applied directly to a silica gel column and eluted with a gradient of 0% to 10% ethyl acetate in dichloromethane. Evaporation of the solvent yielded 9.5 mg of product. MS (ES, m/z) 704.2 [M+H]+.

Workup

  1. washeluted with a gradient of 0% to 10% ethyl acetate in dichloromethane
  2. customEvaporation of the solvent

Sources & evidence

ORD record
ord-aee3980a388c4aa88acab2327443d4f6
Source dataset
uspto-grants-2016_04
Patent number
US09301951B2

Reaction notes

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