Chloroform → 8-[(4-Hydroxybenzyl)amino]-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide

HRID 875129Notes

Reaction equation

HRID 875129 reaction equation
C[O:2][C:3]1[CH:27]=[CH:26][C:6]([CH2:7][NH:8][C:9]2[N:18]=[CH:17][C:16]3[CH2:15][CH2:14][C:13]4[C:19]([C:23]([NH2:25])=[O:24])=[N:20][N:21]([CH3:22])[C:12]=4[C:11]=3[N:10]=2)=[CH:5][CH:4]=1.C(Cl)(Cl)Cl>[OH-].[NH4+]>[OH:2][C:3]1[CH:27]=[CH:26][C:6]([CH2:7][NH:8][C:9]2[N:18]=[CH:17][C:16]3[CH2:15][CH2:14][C:13]4[C:19]([C:23]([NH2:25])=[O:24])=[N:20][N:21]([CH3:22])[C:12]=4[C:11]=3[N:10]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 6212ChloroformHCID 451418008-[(4-Methoxybenzyl)amino]-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide

Product 1

HCID 574441408-[(4-Hydroxybenzyl)amino]-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamideYield 53%

Reagents, catalysts & solvents 1

HCID 14923Ammonium HydroxideSolvent

Procedure

To a well stirred solution of 8-[(4-methoxybenzyl)amino]-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide (242 mg, 0.7 mmol) in chloroform (30 mL) boron tribromide (1 M in dichloromethane, 5.12 mL, 5.1 mmol) was added dropwise over a 5 minutes period, at room temperature. The mixture was heated to reflux for 8 hours. A solution of 10% aqueous ammonium hydroxide (30 mL) was added dropwise at 0° C. over a 10 minutes period. A precipitate was formed and, after 2 hours, it was filtered and washed with water and dried at 40° C. under vacuum. There were obtained 130 mg of the title compound.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 8 hours
  3. customA precipitate was formed and, after 2 hours
  4. filtrationit was filtered
  5. washwashed with water
  6. customdried at 40° C. under vacuum

Sources & evidence

ORD record
ord-9ec78a4b22f54ac1929fcef815f1a445
Source dataset
uspto-grants-2015_03
Patent number
US08981089B2

Reaction notes

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