3-[(5-Oxo-4,5-dihydropyrazolo[1,5-a]quinazolin-2-yl)methyl]benzonitrile → 2-[3-(Aminomethyl)benzyl]pyrazolo[1,5-a]quinazolin-5(4h)-one

HRID 1927285Notes

Reaction equation

HRID 1927285 reaction equation
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]2[N:12]=[C:13]([CH2:15][C:16]3[CH:17]=[C:18]([CH:21]=[CH:22][CH:23]=3)[C:19]#[N:20])[CH:14]=[C:4]2[NH:3]1>N.CO.[Ni]>[NH2:20][CH2:19][C:18]1[CH:17]=[C:16]([CH:23]=[CH:22][CH:21]=1)[CH2:15][C:13]1[CH:14]=[C:4]2[NH:3][C:2](=[O:1])[C:11]3[C:6]([N:5]2[N:12]=1)=[CH:7][CH:8]=[CH:9][CH:10]=3

Participants

4

Reactant 1

HCID 1359396473-[(5-Oxo-4,5-dihydropyrazolo[1,5-a]quinazolin-2-yl)methyl]benzonitrile

Product 1

HCID 1359396482-[3-(Aminomethyl)benzyl]pyrazolo[1,5-a]quinazolin-5(4h)-one

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 21705897Ammonia methanolSolvent

Procedure

A mixture of Example 62 (0.32 g, 1.066 mmol) and 3 g raney-nickel in methanol ammonia (30 mL) was stirred under a hydrogen atmosphere at 60 psi for 3.5 hr. The mixture was filtered then evaporated and purified by chromatography on silica gel with 10% MeOH/CH2Cl2 to provide the desired product. 1H NMR (400 MHz, DMSO-d6) δ ppm 3.17 (s, 1 H) 3.71 (s, 2 H) 3.97 (s, 2 H) 5.66 (s, 1 H) 7.14-7.20 (m, 2 H) 7.22-7.29 (m, 2 H) 7.42-7.47 (m, 1 H) 7.82-7.87 (m, 1 H) 8.03 (d, J=8.29 Hz, 1 H) 8.11 (dd, J=7.98, 1.53 Hz, 1 H).

Workup

  1. filtrationThe mixture was filtered
  2. customthen evaporated
  3. custompurified by chromatography on silica gel with 10% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-a22b221c7eb0430eb73da04d4eb2694c
Source dataset
uspto-grants-2012_05
Patent number
US08183250B2

Reaction notes

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