HCID 59404996, compound → HCID 59405010, compound

HRID 1672196Notes

Reaction equation

HRID 1672196 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-60121529f6a1430985682ce19b2ff72e
Source dataset
uspto-grants-2011_08
Patent number
US07998952B2

Reaction notes

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