Diethyl Ether → Ethyl 8-{[1-(tert-butoxycarbonyl)pyrrolidin-3-yl]amino}-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxylate

HRID 875107Notes

Reaction equation

HRID 875107 reaction equation
[CH3:1][N:2]1[C:14]2[C:13]3[N:12]=[C:11](OS(C(F)(F)F)(=O)=O)[N:10]=[CH:9][C:8]=3[CH2:7][CH2:6][C:5]=2[C:4]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[N:3]1.[NH2:28][CH:29]1[CH2:33][CH2:32][N:31]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:30]1.C(OCC)C>O1CCOCC1>[C:37]([O:36][C:34]([N:31]1[CH2:32][CH2:33][CH:29]([NH:28][C:11]2[N:10]=[CH:9][C:8]3[CH2:7][CH2:6][C:5]4[C:4]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[N:3][N:2]([CH3:1])[C:14]=4[C:13]=3[N:12]=2)[CH2:30]1)=[O:35])([CH3:40])([CH3:38])[CH3:39]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 27563701-Boc-3-aminopyrrolidineHCID 45141798Ethyl 1-methyl-8-([(trifluoromethyl)sulfonyl]oxy}-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxylate

Product 1

HCID 57444099Ethyl 8-{[1-(tert-butoxycarbonyl)pyrrolidin-3-yl]amino}-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxylateYield 88%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 1.5 g (3.7 mmol) of ethyl 1-methyl-8-{[(trifluoromethyl)sulfonyl]oxy}-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxylate in 150 mL of anhydrous dioxane, 756 mg (4.1 mmol) of tert-butyl 3-aminopyrrolidine-1-carboxylate were added. The reaction mixture was stirred at room temperature overnight. The solvent was then removed under reduced pressure, the residue redissolved with dichloromethane and washed with water. The organic layer was dried over sodium sulfate and evaporated. 1.2 g (88% yield) of the title compound was collected by filtration after trituration with diethylether.

Workup

  1. customThe solvent was then removed under reduced pressure
  2. dissolutionthe residue redissolved with dichloromethane
  3. washwashed with water
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-a9c39e9f281a4ccab6a4fd796398474c
Source dataset
uspto-grants-2015_03
Patent number
US08981089B2

Reaction notes

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