HCID 59404996, compound → HCID 59405010, compound

HRID 2387985Notes

Reaction equation

HRID 2387985 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][C:5]2[CH2:6][C:7](=[O:24])[NH:8][C:9]3[CH:16]=[C:15]([Cl:17])[C:14]([C:18]#[C:19][CH2:20][N:21]([CH3:23])[CH3:22])=[CH:13][C:10]=3[C:11]=2[N:12]=1>O.C1COCC1.[Ni]>[NH2:1][C:2]1[N:3]=[CH:4][C:5]2[CH2:6][C:7](=[O:24])[NH:8][C:9]3[CH:16]=[C:15]([Cl:17])[C:14]([CH2:18][CH2:19][CH2:20][N:21]([CH3:22])[CH3:23])=[CH:13][C:10]=3[C:11]=2[N:12]=1

Participants

5

Reactant 1

HCID 59404996HCID 59404996, compound

Product 1

HCID 59405010HCID 59405010, compoundYield 52%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A slurry of Raney Ni (3.0 mL) in water was added to 2-amino-9-chloro-10-[3-(dimethylamino)prop-1-yn-1-yl]-5,7-dihydro-6H-pyrimido[5,4-d][1]benzazepin-6-one (0.30 g, 0.88 mmol) in THF (6 mL). The reaction mixture was allowed to stir under an atmosphere of H2 at rt overnight. The reaction mixture was filtered over Celite and the filter cake was washed with THF. The filtrate was concentrated and the resulting solid was triturated with MeOH, diethyl ether, and hexanes. The solid was collected via suction filtration to give 2-amino-9-chloro-10-[3-(dimethylamino)propyl]-5,7-dihydro-6H-pyrimido[5,4-d][1]benzazepin-6-one (0.158 g, 52%) as a light yellow solid. LCMS (FA): m/z=346 (M+H).

Workup

  1. filtrationThe reaction mixture was filtered over Celite
  2. washthe filter cake was washed with THF
  3. concentrationThe filtrate was concentrated
  4. customthe resulting solid was triturated with MeOH, diethyl ether, and hexanes
  5. filtrationThe solid was collected via suction filtration

Sources & evidence

ORD record
ord-202412437a8b481bb3e751cac62d1931
Source dataset
uspto-grants-2012_09
Patent number
US08268992B2

Reaction notes

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