Diethyl Ether → HCID 57531700, compound

HRID 1455111Notes

Reaction equation

HRID 1455111 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:26]3[C:25]4[N:24]=[C:23]([NH:27][CH:28]5[CH2:32][CH2:31][CH2:30][CH2:29]5)[N:22]=[CH:21][C:20]=4[CH2:19][CH2:18][C:17]=3[C:16]([C:33]([NH2:35])=[O:34])=[N:15]2)[CH2:10][CH2:9]1)C1C=CC=CC=1.C(OCC)C>C(O)(=O)C.O=[Pt]=O>[CH:28]1([NH:27][C:23]2[N:22]=[CH:21][C:20]3[CH2:19][CH2:18][C:17]4[C:16]([C:33]([NH2:35])=[O:34])=[N:15][N:14]([CH:11]5[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]5)[C:26]=4[C:25]=3[N:24]=2)[CH2:29][CH2:30][CH2:31][CH2:32]1

Participants

5

Reactant 2

HCID 3283Diethyl EtherHCID 57444107HCID 57444107, compound

Product 1

HCID 57531700HCID 57531700, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolvent

Procedure

500 mg (1.1 mmol) of 1-(1-benzylpiperidin-4-yl)-8-(cyclopentylamino)-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide were dissolved in 50 mL of acetic acid and 50 mg of PtO2 were added. The mixture was submitted to hydrogenation at 60 psi at room temperature. After 12 hors the catalyst was filtered on celite and the filtrate evaporated. The residue was redissolved with dicholoromethane and washed with aqueous NaHCO3. The organic layer was dried over sodium sulfate and the solvent removed under reduced pressure. The title compound (80% yield) was collected by filtration after trituration with diethylether.

Workup

  1. customwas submitted to hydrogenation at 60 psi at room temperature
  2. filtrationAfter 12 hors the catalyst was filtered on celite
  3. customthe filtrate evaporated
  4. dissolutionThe residue was redissolved with dicholoromethane
  5. washwashed with aqueous NaHCO3
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-2db5676eadca4fe2baa157cce7125e52
Source dataset
uspto-grants-2009_01
Patent number
US07482354B2

Reaction notes

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