Water → HCID 59541729, compound

HRID 215769Notes

Reaction equation

HRID 215769 reaction equation
ClC([C:7]1[CH:8]=[N:9][N:10]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][CH2:21][N:22]3[CH2:26][CH2:25][CH2:24][C@H:23]3[CH3:27])=[CH:14][CH:13]=2)[CH:11]=1)CCC[NH-].[H-].[Na+].[OH2:30]>O1CCCC1>[CH3:27][C@@H:23]1[CH2:24][CH2:25][CH2:26][N:22]1[CH2:21][CH2:20][CH2:19][O:18][C:15]1[CH:14]=[CH:13][C:12]([N:10]2[CH:11]=[C:7]([N:22]3[CH2:26][CH2:25][CH2:24][C:23]3=[O:30])[CH:8]=[N:9]2)=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24758Sodium hydrideHCID 86646673HCID 86646673, compound

Product 1

HCID 59541729HCID 59541729, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 4-chloro-N-[1-(4-{3-[(2R)-2-methylpyrrolidin-1-yl]propoxy}phenyl)-1H-pyrazol-4-yl]butylamide obtained in Example 29-(2) (0.224 g) in tetrahydrofuran (2.0 mL), sodium hydride (55% in mineral oil, 0.111 g) was added and stirred at room temperature for 30 minutes. The reaction mixture was diluted with water and extracted with chloroform. The organic layer was washed with brine, dried over sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by NH-type silica gel column chromatography (eluting solvent: chloroform:methanol=100:1), and the resulting crystal was washed with diisopropyl ether to give the titled compound (0.127 g) as a light-yellow solid.

Workup

  1. extractionextracted with chloroform
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by NH-type silica gel column chromatography (eluting solvent: chloroform:methanol=100:1)
  6. washthe resulting crystal was washed with diisopropyl ether

Sources & evidence

ORD record
ord-402e00c253fb451da809854e7ec6cc12
Source dataset
uspto-grants-2012_06
Patent number
US08193176B2

Reaction notes

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