Dicyclohexylcarbodiimide → 1-[2-(2-{3-[2-Oxo-2-(pyrrolidin-1-yl)ethyl]pyrrolidin-1-yl}ethyl)phenyl]piperidin-2-one
Reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][CH2:5][CH2:4][N:3]1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH2:14][CH2:15][N:16]1[CH2:20][CH2:19][CH:18]([CH2:21][C:22](O)=[O:23])[CH2:17]1.[NH:25]1[CH2:29][CH2:28][CH2:27][CH2:26]1.C1(N=C=NC2CCCCC2)CCCCC1.OC1C2N=NNC=2C=CC=1.C(N(C(C)C)CC)(C)C>ClCCl>[O:23]=[C:22]([N:25]1[CH2:29][CH2:28][CH2:27][CH2:26]1)[CH2:21][CH:18]1[CH2:19][CH2:20][N:16]([CH2:15][CH2:14][C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[N:3]2[CH2:4][CH2:5][CH2:6][CH2:7][C:2]2=[O:1])[CH2:17]1Participants
7
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
To (1-{2-[2-(2-oxopiperidin-1-yl)phenyl]ethyl}pyrrolidin-3-yl)acetic acid a14-1 (115 mg, 0.348 mmol, 1 eq) and pyrrolidine (32 μl, 0.382 mmol 1.1 eq) in dichloromethane (5 ml) are added dicyclohexylcarbodiimide (79 mg, 0.82 mmol, 1.1 eq), hydroxybenzotriazole (52 mg, 0.382 mmol, 1.1 eq) and diisopropylethylamine (131 μl, 0.731 mmol, 2.1 eq). The reaction mixture is stirred overnight at room temperature, then filtered and concentrated under reduced pressure. The residue is purified by reverse phase chromatography (gradient: CH3CN/H2O/NH4OH from 30/70/0.1 to 60/40/0.1) to afford 9 mg of 1-[2-(2-{3-[2-oxo-2-(pyrrolidin-1-yl)ethyl]pyrrolidin-1-yl}ethyl)phenyl]piperidin-2-one 86 as a yellow oil.
Workup
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customThe residue is purified by reverse phase chromatography (gradient: CH3CN/H2O/NH4OH from 30/70/0.1 to 60/40/0.1)
Sources & evidence
- ORD record
- ord-9889b75340824337a95f65a0c4cd408f
- Source dataset
- uspto-grants-2015_06
- Patent number
- US09067930B2
Reaction notes
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