Sodium Hydroxide → HCID 86597695, compound

HRID 547808Notes

Reaction equation

HRID 547808 reaction equation
[F:1][C:2]([F:47])([F:46])[C:3]1[CH:4]=[C:5]([C:13]([CH3:45])([CH3:44])[C:14]([N:16]([CH3:43])[C:17]2[C:18]([C:35]3[CH:40]=[CH:39][C:38]([F:41])=[CH:37][C:36]=3[CH3:42])=[CH:19][C:20]([N:23]3[CH2:28][CH2:27][CH:26]([CH2:29]OS(C)(=O)=O)[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.[CH3:48][S-:49].[Na+].[OH-].[Na+]>CN(C=O)C>[F:11][C:9]([F:12])([F:10])[C:7]1[CH:6]=[C:5]([C:13]([CH3:45])([CH3:44])[C:14]([N:16]([C:17]2[C:18]([C:35]3[CH:40]=[CH:39][C:38]([F:41])=[CH:37][C:36]=3[CH3:42])=[CH:19][C:20]([N:23]3[CH2:28][CH2:27][CH:26]([CH2:29][S:49][CH3:48])[CH2:25][CH2:24]3)=[N:21][CH:22]=2)[CH3:43])=[O:15])[CH:4]=[C:3]([C:2]([F:1])([F:47])[F:46])[CH:8]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 4378561Sodium methanethiolateHCID 86597696HCID 86597696, compound

Product 1

HCID 86597695HCID 86597695, compoundYield 92.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 0.29 g (0.42 mmol) methanesulfonic acid 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-ylmethyl ester and 44 mg (0.63 mmol) sodium methanethiolate in 8 ml DMF was heated at 80° C. for 30 min. After cooling to room temperature the reaction mixture was treated with a 1 N aqueous sodium hydroxide solution and extracted with three portions of tert-butyl methyl ether. The combined organic extracts were dried over sodium sulphate and concentrated. Flash column chromatography gave 0.25 g (92%) of the title compound as a white solid.

Workup

  1. extractionextracted with three portions of tert-butyl methyl ether
  2. dry with materialThe combined organic extracts were dried over sodium sulphate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-088e42433ac749d5acca24e7a7724c87
Source dataset
uspto-grants-2011_05
Patent number
US07939533B2

Reaction notes

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