8-(cyclohexylamino)-1-methyl-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide → Diethyl Ether

HRID 1455108Notes

Reaction equation

HRID 1455108 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH:10]([NH:13][C:14]2[N:23]=[CH:22][C:21]3[CH2:20][CH2:19][C:18]4[C:24]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[N:25][N:26]([CH3:27])[C:17]=4[C:16]=3[N:15]=2)[CH2:9]1)=O)(C)(C)C.C1(NC2N=CC3C=CC4C(C(N)=O)=NN(C)C=4C=3N=2)CCCCC1>>[CH2:28]([O:30][CH2:31][CH3:32])[CH3:24].[CH3:27][N:26]1[C:17]2[C:16]3[N:15]=[C:14]([NH:13][CH:10]4[CH2:11][CH2:12][NH:8][CH2:9]4)[N:23]=[CH:22][C:21]=3[CH2:20][CH2:19][C:18]=2[C:24]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[N:25]1

Participants

4

Reactant 2

HCID 116527368-(cyclohexylamino)-1-methyl-1H-pyrazolo[4,3-h]quinazoline-3-carboxamideHCID 57444099Ethyl 8-{[1-(tert-butoxycarbonyl)pyrrolidin-3-yl]amino}-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxylate

Product 2

HCID 3283Diethyl EtherYield 829.5%HCID 68958913Ethyl 1-methyl-8-(pyrrolidin-3-ylamino)-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxylate

Procedure

A solution of 110 mg (0.27 mmol) of ethyl 8-{[1-(tert-butoxycarbonyl)pyrrolidin-3-yl]amino}-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxylate in a mixture dichoromethane-trifluoroacetic acid 9/1 was stirred at room temperature for 6 hours. The solvent was then removed in vacuo and the resulting oil taken up with dichloromethane and washed with aqueous NaHCO3. The organic layer was dried over Na2SO4 and evaporated. The residue was triturated with diethylether giving 83 mg (60% yield) of the title compound.

Workup

  1. customThe solvent was then removed in vacuo
  2. washwashed with aqueous NaHCO3
  3. dry with materialThe organic layer was dried over Na2SO4
  4. customevaporated

Sources & evidence

ORD record
ord-334455adbb464d2fb2993ddd8336beb4
Source dataset
uspto-grants-2009_01
Patent number
US07482354B2

Reaction notes

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