Water → 4-({3-[(2,6-Diethylphenyl)carbamoyl]-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazolin-8-yl}amino)-3-methoxybenzoic acid

HRID 81957Notes

Reaction equation

HRID 81957 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][CH3:10])[C:4]=1[NH:11][C:12]([C:14]1[C:18]2[CH2:19][CH2:20][C:21]3[CH:22]=[N:23][C:24]([NH:27][C:28]4[CH:40]=[CH:39][C:31]([C:32]([O:34]C(C)(C)C)=[O:33])=[CH:30][C:29]=4[O:41][CH3:42])=[N:25][C:26]=3[C:17]=2[N:16]([CH3:43])[N:15]=1)=[O:13])[CH3:2].O>CN(C)C=O.FC(F)(F)C(O)=O>[CH2:9]([C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([CH2:1][CH3:2])[C:4]=1[NH:11][C:12]([C:14]1[C:18]2[CH2:19][CH2:20][C:21]3[CH:22]=[N:23][C:24]([NH:27][C:28]4[CH:40]=[CH:39][C:31]([C:32]([OH:34])=[O:33])=[CH:30][C:29]=4[O:41][CH3:42])=[N:25][C:26]=3[C:17]=2[N:16]([CH3:43])[N:15]=1)=[O:13])[CH3:10]

Participants

5

Reactant 2

HCID 962WaterHCID 44556274HCID 44556274, compound

Product 1

HCID 445562754-({3-[(2,6-Diethylphenyl)carbamoyl]-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazolin-8-yl}amino)-3-methoxybenzoic acidYield 99.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of tert-butyl 4-({3-[(2,6-diethylphenyl)carbamoyl]-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazolin-8-yl}amino)-3-methoxybenzoate (500 mg, 0.857 mmol) in dimethylformamide (8 mL), trifluoro acetic acid (0.600 mL), were added. The mixture was stirred at room temperature overnight. Water was added and the mixture extracted with ethylacetate. The organic solvent evaporated to dryness. To give 450 mg of the title compound in quantitative yield.

Workup

  1. extractionthe mixture extracted with ethylacetate
  2. customThe organic solvent evaporated to dryness

Sources & evidence

ORD record
ord-f80374362ca74d7685d956d32bad6840
Source dataset
uspto-grants-2014_09
Patent number
US08846701B2

Reaction notes

Loading…