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

HRID 474384Notes

Reaction equation

HRID 474384 reaction equation
COCCC(NC1C2C(=C(C(OC)=O)C=CC=2)N=CN=1)C1C=CC=C([N+]([O-])=O)C=1.N.[CH3:31][O:32][CH2:33][CH2:34][CH:35]([NH:45][C:46]1[C:55]2[C:50](=[C:51]([C:56]([NH2:58])=[O:57])[CH:52]=[CH:53][CH:54]=2)[N:49]=[CH:48][N:47]=1)[C:36]1[CH:41]=[CH:40][CH:39]=[C:38]([N+:42]([O-])=O)[CH:37]=1>CO.[Pd]>[NH2:42][C:38]1[CH:37]=[C:36]([CH:35]([NH:45][C:46]2[C:55]3[C:50](=[C:51]([C:56]([NH2:58])=[O:57])[CH:52]=[CH:53][CH:54]=3)[N:49]=[CH:48][N:47]=2)[CH2:34][CH2:33][O:32][CH3:31])[CH:41]=[CH:40][CH:39]=1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 66763230Methyl 4-{[3-methoxy-1-(3-nitrophenyl)propyl]amino}quinazoline-8-carboxylateHCID 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-58534586d76f47ff9e7c71d26678faee
Source dataset
uspto-grants-2014_01
Patent number
US08637532B2

Reaction notes

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