Ammonia → 4-{[1-(3-Aminophenyl)-3-methoxypropyl]amino}quinazoline-8-carboxamide

HRID 578620Notes

Reaction equation

HRID 578620 reaction equation
N.[CH3:2][O:3][CH2:4][CH2:5][CH:6]([NH:16][C:17]1[C:26]2[C:21](=[C:22]([C:27]([NH2:29])=[O:28])[CH:23]=[CH:24][CH:25]=2)[N:20]=[CH:19][N:18]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-])=O)[CH:8]=1>CO.[Pd]>[NH2:13][C:9]1[CH:8]=[C:7]([CH:6]([NH:16][C:17]2[C:26]3[C:21](=[C:22]([C:27]([NH2:29])=[O:28])[CH:23]=[CH:24][CH:25]=3)[N:20]=[CH:19][N:18]=2)[CH2:5][CH2:4][O:3][CH3:2])[CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 667634174-{[3-Methoxy-1-(3-nitrophenyl)propyl]amino}quinazoline-8-carboxamide

Product 1

HCID 667632604-{[1-(3-Aminophenyl)-3-methoxypropyl]amino}quinazoline-8-carboxamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

To a solution of methyl 4-{([3-methoxy-1-(3-nitrophenyl)propyl]amino}quinazoline-8-carboxylate (1.74 g; 4.40 mmol) in methanol was added methanolic ammonia (7N) (30.00 ml; 7.00 M; 210.00 mmol) and stirred for 3 days. Insoluble material was removed by filtration and concentrated. The crude 4-{[3-methoxy-1-(3-nitrophenyl)propyl]amino}quinazoline-8-carboxamide (1.5 g) of was used for the next reaction without further purification. To a solution of 4-{[3-methoxy-1-(3-nitrophenyl)propyl]amino}quinazoline-8-carboxamide (1.5 g) in MeOH (30 mL) was added palladium on active carbon (400 mg) and the mixture was hydrogenated at 40 psi for 4 h. Filtered through a pad of Celite and the solvent was removed. The crude product (1.2 g) was used as such for amide formation. LCMS [352 (M+1)].

Workup

  1. customInsoluble material was removed by filtration
  2. concentrationconcentrated
  3. customThe crude 4-{[3-methoxy-1-(3-nitrophenyl)propyl]amino}quinazoline-8-carboxamide (1.5 g) of was used for the next reaction without further purification
  4. waitthe mixture was hydrogenated at 40 psi for 4 h
  5. filtrationFiltered through a pad of Celite
  6. customthe solvent was removed

Sources & evidence

ORD record
ord-4839131459fe42168d7ee1b956152c31
Source dataset
uspto-grants-2015_05
Patent number
US09040560B2

Reaction notes

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