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

HRID 875115Notes

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

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-05ea171e326c4655bb0b19a1648514dc
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08981089B2

Reaction notes

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