Diisopropylethylamine → 1-(6-Carbamoylpyridin-3-yl)pyrrolidin-3-yl 4-nitrophenyl carbonate

HRID 1504605Notes

Reaction equation

HRID 1504605 reaction equation
[OH:1][CH:2]1[CH2:6][CH2:5][N:4]([C:7]2[CH:8]=[CH:9][C:10]([C:13]([NH2:15])=[O:14])=[N:11][CH:12]=2)[CH2:3]1.[C:16](Cl)(=[O:27])[O:17][C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=1.CCN(C(C)C)C(C)C>N1C=CC=CC=1>[C:16](=[O:27])([O:17][C:18]1[CH:19]=[CH:20][C:21]([N+:24]([O-:26])=[O:25])=[CH:22][CH:23]=1)[O:1][CH:2]1[CH2:6][CH2:5][N:4]([C:7]2[CH:12]=[N:11][C:10]([C:13](=[O:14])[NH2:15])=[CH:9][CH:8]=2)[CH2:3]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 821294-Nitrophenyl chloroformateHCID 867300615-(3-Hydroxypyrrolidin-1-yl)picolinamide

Product 1

HCID 867300621-(6-Carbamoylpyridin-3-yl)pyrrolidin-3-yl 4-nitrophenyl carbonateYield 56%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 5-(3-hydroxypyrrolidin-1-yl)picolinamide (1 g, 4.83 mmol) and 4-nitrophenyl carbonochloridate (1.46 g, 8.3 mmol) in pyridine (30 mL) was added DIPEA (1.25 g, 11 mmol) and the resulting mixture was stirred at rt for 3 days. The precipitate was collected by filtration and the cake was washed with DCM (20 mL) to give the desired compound (1.0 g, 56%) as a pale yellow solid. [LCMS: RtA=1.48 min, m/z 373.2 [M+H]+].

Workup

  1. filtrationThe precipitate was collected by filtration
  2. washthe cake was washed with DCM (20 mL)

Sources & evidence

ORD record
ord-5024367d6098498f9139e44ffa2c0ef3
Source dataset
uspto-grants-2015_12
Patent number
US09216182B2

Reaction notes

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