HCID 51030176, compound → HCID 67055897, compound

HRID 2036847Notes

Reaction equation

HRID 2036847 reaction equation
[C:1]1([C:7]2[CH:16]=[CH:15][CH:14]=[C:13]3[C:8]=2[C:9]([NH:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=2)=[N:10][C:11]([C:17]2([C:20]#[N:21])[CH2:19][CH2:18]2)=[N:12]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>CO.N.[Ni]>[NH2:21][CH2:20][C:17]1([C:11]2[N:10]=[C:9]([NH:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=3)[C:8]3[C:13](=[CH:14][CH:15]=[CH:16][C:7]=3[C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[N:12]=2)[CH2:18][CH2:19]1

Participants

4

Reactant 1

HCID 51030176HCID 51030176, compound

Product 1

HCID 67055897HCID 67055897, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 21705897Ammonia methanolSolvent

Procedure

To a solution of 1-(5-phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl)cyclopropanecarbonitrile (Example 207, 0.6 g, 2 mmol) in 7 M ammonia methanol (10 mL) was added Ra—Ni (200 mg). The resulting slurry was stirred under hydrogen atmosphere for 16 h. After this time, the reaction mixture was filtered and filtrate was concentrated under reduced pressure to yield 2-(1-(aminomethyl)cyclopropyl)-5-phenyl-N-(pyridin-2-ylmethyl)quinazolin-4-amine (380 mg, 63% yield), which was used without further purification.

Workup

  1. filtrationAfter this time, the reaction mixture was filtered
  2. concentrationfiltrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-1a061bbef4254ea994e1b95d88167c7d
Source dataset
uspto-grants-2013_11
Patent number
US08575184B2

Reaction notes

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