Formic Acid → 1-methyl-8-(piperidin-4-ylamino)-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide

HRID 44606Notes

Reaction equation

C([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[N:24]=[CH:23][C:22]3[CH2:21][CH2:20][C:19]4[C:25]([C:29]([NH2:31])=[O:30])=[N:26][N:27]([CH3:28])[C:18]=4[C:17]=3[N:16]=2)[CH2:10][CH2:9]1)C1C=CC=CC=1.C(O)=O>C(O)C.[Pd]>[CH3:28][N:27]1[C:18]2[C:17]3[N:16]=[C:15]([NH:14][CH:11]4[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]4)[N:24]=[CH:23][C:22]=3[CH2:21][CH2:20][C:19]=2[C:25]([C:29]([NH2:31])=[O:30])=[N:26]1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 1 g (2.4 mmol) of 8-[(1-benzylpiperidin-4-yl)amino]-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide in 90 mL of absolute ethanol 1 g of palladium on charcoal 10% w and 30 mL of 98% formic acid were added. The resulting mixture was stirred at 60° C. for 12 hours. The catalyst was then filtered on celite and the filtrate evaporated. The crude was purified by chromatography on a silica gel column eluted with a mixture CH2Cl2MeOH-Et3N, giving 350 mg (45% yield) of the title compound.

Workup

filtrationThe catalyst was then filtered on celite
customthe filtrate evaporated
customThe crude was purified by chromatography on a silica gel column
washeluted with a mixture CH2Cl2MeOH-Et3N

Sources & evidence

ORD record: ord-4048ad24ddd0420b8031db95fa414c00
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08541429B2

Reaction notes

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