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

HRID 1455110Notes

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-baeed7c8e7d9489b9f89b52c0d061dae
Source dataset: uspto-grants-2009_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07482354B2

Reaction notes

Loading…