Dimethylformamide → 8-[(1-formylpiperidin-4-yl)amino]-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide
Reaction equation
[CH3:1][N:2]1[C:14]2[C:13]3[N:12]=[C:11]([NH:15][CH:16]4[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]4)[N:10]=[CH:9][C:8]=3[CH2:7][CH2:6][C:5]=2[C:4]([C:22]([NH2:24])=[O:23])=[N:3]1.[Si](Cl)(C(C)(C)C)(C)C.C(N(CC)CC)C.CN(C)[CH:42]=[O:43]>CN(C)C1C=CN=CC=1>[CH:42]([N:19]1[CH2:18][CH2:17][CH:16]([NH:15][C:11]2[N:10]=[CH:9][C:8]3[CH2:7][CH2:6][C:5]4[C:4]([C:22]([NH2:24])=[O:23])=[N:3][N:2]([CH3:1])[C:14]=4[C:13]=3[N:12]=2)[CH2:21][CH2:20]1)=[O:43]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 37.5 °C
Procedure
500 mg (1.53 mmol) of 1-methyl-8-(piperidin-4-ylamino)-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide were dissolved in 10 mL of dimethylformamide, containing 253 mg (1.68 mmol) of tert-butyldimethylsilyl chloride, 0.26 mL of triethylamine and 7 mg of 4-dimethylaminopyridine (0.06 mmol), and the mixture stirred at 35-40° C. for 25 hours under nitrogen. The mixture was then partitioned between dichloromethane and water, the organic layer was separated, washed with brine and dried over sodium sulfate. Evaporation of the volatiles in vacuo afforded 435 mg (80% yield) of the title compound.
Workup
- customThe mixture was then partitioned between dichloromethane and water
- customthe organic layer was separated
- washwashed with brine
- dry with materialdried over sodium sulfate
- customEvaporation of the volatiles in vacuo
Sources & evidence
- ORD record
- ord-76dd4861cff74f1fbd0f2e2967bb2946
- Source dataset
- uspto-grants-2013_09
- Patent number
- US08541429B2
Reaction notes
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