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

HRID 1026891Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[N:4][N:5]2[C:10](Cl)=[C:9]([C:12]([N:14]3[CH2:19][CH2:18][CH:17]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[CH2:16][CH2:15]3)=[O:13])[CH:8]=[N:7][C:6]=12.[CH2:26]([NH2:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O.O>CN1CCCC1=O>[CH2:26]([NH:33][C:10]1[N:5]2[N:4]=[CH:3][C:2]([Br:1])=[C:6]2[N:7]=[CH:8][C:9]=1[C:12]([N:14]1[CH2:19][CH2:18][CH:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:16][CH2:15]1)=[O:13])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

Conditions

Temperature: 70 °C

Procedure

3-Bromo-7-chloro-6-(4-phenylpiperidine-1-carbonyl)pyrazolo[1,5-a]pyrimidine (3.0 g, 7.2 mmol) obtained in step 3 was dissolved in N-methylpyrrolidinone (30 mL), benzylamine (2.0 mL, 17.9 mmol) was added, and the mixture was stirred at 70° C. for 2 hr. 10% Aqueous citric acid solution (10 mL) and water (100 mL) were added to the reaction mixture, and the mixture was stirred at room temperature for 1 hr. The precipitate was collected by filtration, and washed with water (50 mL) to give the title compound (3.2 g, 90%).

Workup

stirringthe mixture was stirred at room temperature for 1 hr
filtrationThe precipitate was collected by filtration
washwashed with water (50 mL)

Sources & evidence

ORD record: ord-df7ac02a16324438a42f46b33da73cba
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08729264B2

Reaction notes

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