Dimethyl Sulfoxide → HCID 21018324, compound

HRID 1744671Notes

Reaction equation

HRID 1744671 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([N:18]2[C:22]([CH3:23])=[C:21]([C:24]([NH:26][C:27]3[CH:32]=[CH:31][C:30]([N:33]4[CH2:38][CH2:37][CH:36]([N:39]5[CH2:44][CH2:43][CH:42]([OH:45])[CH2:41][CH2:40]5)[CH2:35][CH2:34]4)=[C:29]([C:46]#[N:47])[CH:28]=3)=[O:25])[CH:20]=[N:19]2)=[CH:14][CH:13]=1.[OH-].[Na+]>C(Cl)Cl.C(N(CC)CC)C>[Cl:11][C:12]1[CH:13]=[CH:14][C:15]([N:18]2[C:22]([CH3:23])=[C:21]([C:24]([NH:26][C:27]3[CH:32]=[CH:31][C:30]([N:33]4[CH2:38][CH2:37][CH:36]([N:39]5[CH2:40][CH2:41][C:42](=[O:45])[CH2:43][CH2:44]5)[CH2:35][CH2:34]4)=[C:29]([C:46]#[N:47])[CH:28]=3)=[O:25])[CH:20]=[N:19]2)=[CH:16][CH:17]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 14798Sodium HydroxideHCID 65578Oxalyl chlorideHCID 22228071HCID 22228071, compound

Product 1

HCID 21018324HCID 21018324, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of oxalyl chloride (0.1 ml) and dimethyl sulfoxide (0.2 ml) in methylene chloride (30 ml) were added under ice-cooling 1-(4-chlorophenyl)-N-[3-cyano-4-[4-(4-hydroxypiperidin-1-yl)piperidin-1-yl]phenyl]-5-methylpyrazole-4-carboxamide synthesized in Example 189 and triethylamine (0.9 ml), and the mixture was stirred at the same temperature for 1 h. To a reaction mixture was added aqueous sodium hydroxide solution. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (mobile phase: chloroform:methanol=20:1) to give the title compound (0.2 g), melting point: 213° C.

Workup

  1. washThe organic layer was washed with saturated brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (mobile phase: chloroform:methanol=20:1)

Sources & evidence

ORD record
ord-aa17ba2345254e688e124e99c1c0ef01
Source dataset
uspto-grants-2006_03
Patent number
US07015218B1

Reaction notes

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