Pyrrolidine → tert-butyl 4-[3-carbamoyl-8-(pyrrolidin-1-yl)-1H-pyrazolo[4,3-h]quinazolin-1-yl]piperidine-1-carboxylate

HRID 45801Notes

Reaction equation

HRID 45801 reaction equation
[C:1]([C:4]1[C:8]2[CH:9]=[CH:10][C:11]3[CH:12]=[N:13][C:14](S(C)(=O)=O)=[N:15][C:16]=3[C:7]=2[N:6]([CH:21]2[CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:23][CH2:22]2)[N:5]=1)(=[O:3])[NH2:2].[NH:34]1[CH2:38][CH2:37][CH2:36][CH2:35]1>C1COCC1>[C:1]([C:4]1[C:8]2[CH:9]=[CH:10][C:11]3[CH:12]=[N:13][C:14]([N:34]4[CH2:38][CH2:37][CH2:36][CH2:35]4)=[N:15][C:16]=3[C:7]=2[N:6]([CH:21]2[CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:23][CH2:22]2)[N:5]=1)(=[O:3])[NH2:2]

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 67975337tert-butyl 4-[3-carbamoyl-8-(methylsulfonyl)-1H-pyrazolo[4,3-h]quinazolin-1-yl]piperidine-1-carboxylate

Product 1

HCID 67975453tert-butyl 4-[3-carbamoyl-8-(pyrrolidin-1-yl)-1H-pyrazolo[4,3-h]quinazolin-1-yl]piperidine-1-carboxylateYield 51.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl 4-[3-carbamoyl-8-(methylsulfonyl)-1H-pyrazolo[4,3-h]quinazolin-1-yl]piperidine-1-carboxylate 30 mg (0.063 mmol) in THF (3 ml), pyrrolidine 70 μl (1 mmol) was added. The solution was stirred at room temperature for 1 hour and monitored by LC/MS. The reaction mixture was cooled to room temperature; the separated solid was filtered and washed with diethyl ether to afford tert-butyl 4-[3-carbamoyl-8-(pyrrolidin-1-yl)-1H-pyrazolo[4,3-h]quinazolin-1-yl]piperidine-1-carboxylate 15 mg (50%). LC/MS (m/z): 475.0 [M+H]+, HPLC (254 nm) method 4 Rt 2.01 min.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationthe separated solid was filtered
  3. washwashed with diethyl ether

Sources & evidence

ORD record
ord-2036c8af6728491eb9d4a10fac43048d
Source dataset
uspto-grants-2013_09
Patent number
US08541576B2

Reaction notes

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