HCID 66933545, compound → HCID 58186874, compound

HRID 1928650Notes

Reaction equation

HRID 1928650 reaction equation
[CH3:1][CH:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([N:17]2[CH:21]=[C:20]([NH:22][C:23](=[O:29])[CH2:24][CH2:25][C:26]([OH:28])=O)[CH:19]=[N:18]2)=[CH:13][CH:12]=1>C(OC(=O)C)(=O)C.C(=O)(O)[O-].[Na+]>[CH3:1][CH:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([N:17]2[CH:21]=[C:20]([N:22]3[C:26](=[O:28])[CH2:25][CH2:24][C:23]3=[O:29])[CH:19]=[N:18]2)=[CH:13][CH:12]=1

Participants

4

Reactant 1

HCID 66933545HCID 66933545, compound

Product 1

HCID 58186874HCID 58186874, compound

Reagents, catalysts & solvents 2

HCID 7918Acetic AnhydrideSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A solution of 1-{4-[3-(2-methylpyrrolidin-1-yl)propoxy]phenyl}-1H-pyrazol-4-ylamine obtained in the same manner as shown in Example 29-(1) (0.186 g) and succinic anhydride (0.074 g) in toluene (12 mL) was stirred under heating at reflux for 4 hours. The reaction mixture was cooled in an ice bath, and the precipitated crystal was collected by filtration and washed with toluene to give N-(1-{4-[3-(2-methylpyrrolidin-1-yl)propoxy]phenyl}-1H-pyrazol-4-yl)succinamic acid (0.191 g) as a colorless powder. A suspension of N-(1-{4-[3-(2-methylpyrrolidin-1-yl)propoxy]phenyl}-1H-pyrazol-4-yl)succinamic acid thus obtained (0.108 g) in acetic anhydride (5.4 mL) was stirred under heating at reflux for 30 minutes. The reaction mixture was cooled to room temperature, diluted with saturated aqueous sodium bicarbonate and extracted with chloroform. The organic layer was dried over sodium sulfate and concentrated under reduced pressure, and the resulting residue was purified by NH-type silica gel column chromatography (eluting solvent: hexane:ethyl acetate=1:1). The resulting solid was washed with diisopropyl ether to give the titled compound (0.044 g) as a colorless powder.

Workup

  1. temperatureunder heating
  2. temperatureat reflux for 30 minutes
  3. extractionextracted with chloroform
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customthe resulting residue was purified by NH-type silica gel column chromatography (eluting solvent: hexane:ethyl acetate=1:1)
  7. washThe resulting solid was washed with diisopropyl ether

Sources & evidence

ORD record
ord-65a6cbf64f164026ac21708753eb9f5b
Source dataset
uspto-grants-2012_05
Patent number
US08183387B2

Reaction notes

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