Triethylamine → HCID 86597696, compound

HRID 1951715Notes

Reaction equation

HRID 1951715 reaction equation
[F:1][C:2]([F:43])([F:42])[C:3]1[CH:4]=[C:5]([C:13]([CH3:41])([CH3:40])[C:14]([N:16]([C:18]2[C:19]([C:32]3[CH:37]=[CH:36][C:35]([F:38])=[CH:34][C:33]=3[CH3:39])=[CH:20][C:21]([N:24]3[CH2:29][CH2:28][CH:27]([CH2:30][OH:31])[CH2:26][CH2:25]3)=[N:22][CH:23]=2)[CH3:17])=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[CH3:44][S:45](Cl)(=[O:47])=[O:46].C(N(CC)CC)C>ClCCl.O>[F:43][C:2]([F:1])([F:42])[C:3]1[CH:4]=[C:5]([C:13]([CH3:40])([CH3:41])[C:14]([N:16]([CH3:17])[C:18]2[C:19]([C:32]3[CH:37]=[CH:36][C:35]([F:38])=[CH:34][C:33]=3[CH3:39])=[CH:20][C:21]([N:24]3[CH2:25][CH2:26][CH:27]([CH2:30][O:31][S:45]([CH3:44])(=[O:47])=[O:46])[CH2:28][CH2:29]3)=[N:22][CH:23]=2)=[O:15])[CH:6]=[C:7]([C:9]([F:10])([F:11])[F:12])[CH:8]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 86597694HCID 86597694, compound

Product 1

HCID 86597696HCID 86597696, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.42 g (0.69 mmol) 2-(3,5-bis-trifluoromethyl-phenyl)-N-[4′-(4-fluoro-2-methyl-phenyl)-4-hydroxymethyl-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-5′-yl]-N-methyl-isobutyramide in 7 ml dichloromethane were added 83 mg (0.72 mmol) methanesulfonyl chloride and 73 mg (0.72 mmol) triethylamine at 0° C. After 30 min 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 0.29 g (63%) 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-88580715983d44c3a74708fec973ac3a
Source dataset
uspto-grants-2013_03
Patent number
US08404708B2

Reaction notes

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