Citric Acid → N-[7-Benzylamino-6-(4-phenylpiperidine-1-carbonyl)pyrazolo[1,5-a]pyrimidine-3-carbonyl]morpholine

HRID 1026898Notes

Reaction equation

HRID 1026898 reaction equation
[CH2:1]([NH:8][C:9]1[N:14]2[N:15]=[CH:16][C:17]([C:18](O)=[O:19])=[C:13]2[N:12]=[CH:11][C:10]=1[C:21]([N:23]1[CH2:28][CH2:27][CH:26]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:25][CH2:24]1)=[O:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:35]1[CH2:40][CH2:39][O:38][CH2:37][CH2:36]1.C1C=CC2N(O)N=NC=2C=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN(C=O)C.O>[CH2:1]([NH:8][C:9]1[N:14]2[N:15]=[CH:16][C:17]([C:18]([N:35]3[CH2:40][CH2:39][O:38][CH2:37][CH2:36]3)=[O:19])=[C:13]2[N:12]=[CH:11][C:10]=1[C:21]([N:23]1[CH2:28][CH2:27][CH:26]([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH2:25][CH2:24]1)=[O:22])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 311Citric AcidHCID 8083MorpholineHCID 757711-HydroxybenzotriazoleHCID 675405547-Benzylamino-6-(4-phenylpiperidine-1-carbonyl)pyrazolo[1,5-a]pyrimidine-3-carboxylic acid

Product 1

HCID 25235821N-[7-Benzylamino-6-(4-phenylpiperidine-1-carbonyl)pyrazolo[1,5-a]pyrimidine-3-carbonyl]morpholine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

7-Benzylamino-6-(4-phenylpiperidine-1-carbonyl)pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (0.08 g, 0.18 mmol) obtained in Example 1, step 5 was dissolved in DMF (1 mL), morpholine (0.02 mL, 0.21 mmol), 3-[(3-dimethylamino)propyl]-1-ethylcarbodiimide hydrochloride (0.04 g, 0.21 mmol) and HOBt (0.03 g, 0.21 mmol) were added, and the mixture was stirred at room temperature for 5 hr. 10% Aqueous citric acid solution (1 mL) and water (10 mL) were added to the reaction mixture, and the mixture was stirred at room temperature for 1 hr. The precipitate was collected by filtration, washed with water (20 mL), and purified by silica gel column chromatography (chloroform/methanol=90/10) to give compound a-11 (0.02 g, 18%).

Workup

  1. stirringthe mixture was stirred at room temperature for 1 hr
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with water (20 mL)
  4. custompurified by silica gel column chromatography (chloroform/methanol=90/10)
  5. customto give compound a-11 (0.02 g, 18%)

Sources & evidence

ORD record
ord-0e41dada5eaa461088d964ea806f997d
Source dataset
uspto-grants-2014_05
Patent number
US08729264B2

Reaction notes

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