Dimethylamine → HCID 86597705, compound

HRID 1951726Notes

Reaction equation

HRID 1951726 reaction equation
[F:1][C:2]([F:45])([F:44])[C:3]1[CH:4]=[C:5]([C:13]([CH3:43])([CH3:42])[C:14]([N:16]([CH3:41])[C:17]2[C:18]([C:33]3[CH:38]=[CH:37][C:36]([F:39])=[CH:35][C:34]=3[CH3:40])=[CH:19][C:20]([N:23]3[CH2:28][CH2:27][CH:26]([S:29](O)(=[O:31])=[O:30])[CH2:25][CH2:24]3)=[N:21][CH:22]=2)=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.C(Cl)(=O)C(Cl)=O.[CH3:52][NH:53][CH3:54]>ClCCl.CN(C=O)C.O>[F:12][C:9]([F:10])([F:11])[C:7]1[CH:6]=[C:5]([C:13]([CH3:43])([CH3:42])[C:14]([N:16]([C:17]2[C:18]([C:33]3[CH:38]=[CH:37][C:36]([F:39])=[CH:35][C:34]=3[CH3:40])=[CH:19][C:20]([N:23]3[CH2:28][CH2:27][CH:26]([S:29](=[O:31])(=[O:30])[N:53]([CH3:54])[CH3:52])[CH2:25][CH2:24]3)=[N:21][CH:22]=2)[CH3:41])=[O:15])[CH:4]=[C:3]([C:2]([F:45])([F:1])[F:44])[CH:8]=1

Participants

7

Reactant 3

HCID 674DimethylamineHCID 65578Oxalyl chlorideHCID 86597706HCID 86597706, compound

Product 1

HCID 86597705HCID 86597705, compoundYield 69%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.13 g (0.19 mmol) 5′-{[2-(3,5-bis-trifluoromethyl-phenyl)-2-methyl-propionyl]-methyl-amino}-4′-(4-fluoro-2-methyl-phenyl)-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-sulfonic acid in 2 ml dichloromethane were added 0.33 ml (0.39 mmol) oxalyl chloride and one drop of DMF at 0° C. After 30 min the reaction mixture was allowed to warm to room temperature during 2 h. To the yellow reaction mixture were added 1.8 ml (20 mmol) of an aqueous solution of dimethylamine (60%). After 1 h the reaction mixture was diluted with water and extracted with three portions of dichloromethane. The combined organic extracts were dried over sodium sulphate and concentrated. Flash column chromatography gave 92 mg (69%) of the title compound as a white solid.

Workup

  1. extractionextracted with three portions of dichloromethane
  2. dry with materialThe combined organic extracts were dried over sodium sulphate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-9f55672622fb4970a396511dd5553717
Source dataset
uspto-grants-2013_03
Patent number
US08404708B2

Reaction notes

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