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

HRID 1026893Notes

Reaction equation

HRID 1026893 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.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH3:47][S:48]([NH2:51])(=[O:50])=[O:49].C1CCN2C(=NCCC2)CC1.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]([NH:51][S:48]([CH3:47])(=[O:50])=[O:49])=[O:19])=[C:13]2[N:12]=[CH:11][C:10]=1[C:21]([N:23]1[CH2:24][CH2:25][CH:26]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:27][CH2:28]1)=[O:22])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 5

HCID 311Citric AcidHCID 682631,1'-CarbonyldiimidazoleHCID 72879MethanesulfonamideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 675405547-Benzylamino-6-(4-phenylpiperidine-1-carbonyl)pyrazolo[1,5-a]pyrimidine-3-carboxylic acid

Product 1

HCID 67539984N-[7-Benzylamino-6-(4-phenylpiperidine-1-carbonyl)pyrazolo[1,5-a]pyrimidine-3-carbonyl]methanesulfonamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

7-Benzylamino-6-(4-phenylpiperidine-1-carbonyl)pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (0.9 g, 1.9 mmol) obtained in step 5 was dissolved in DMF (15 mL), 1,1′-carbonyldiimidazole (1.2 g, 7.6 mmol) was added, and the mixture was stirred at room temperature for 2 hr. Methanesulfonamide (0.9 g, 9.5 mmol) and DBU (1.4 g, 9.5 mmol) were added to the reaction mixture, and the mixture was stirred at 60° C. for 1 hr. 10% Aqueous citric acid solution (5 mL) and water (60 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 (50 mL), and purified by silica gel column chromatography (chloroform/methanol=95/5) to give compound a-1 (0.8 g, 81%).

Workup

  1. stirringthe mixture was stirred at 60° C. for 1 hr
  2. stirringthe mixture was stirred at room temperature for 1 hr
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with water (50 mL)
  5. custompurified by silica gel column chromatography (chloroform/methanol=95/5)
  6. customto give compound a-1 (0.8 g, 81%)

Sources & evidence

ORD record
ord-823b76e55b0648aa9e5d2139d0a62b71
Source dataset
uspto-grants-2014_05
Patent number
US08729264B2

Reaction notes

Loading…