Cyclohexanecarbonyl chloride → N-(1-benzyl-3-methylpyrrolidin-3-yl)-N-[(1-methyl-2-oxo-1,2-dihydroquinolin-3-yl)methyl]cyclohexanecarboxamide

HRID 1943030Notes

Reaction equation

HRID 1943030 reaction equation
[CH2:1]([N:8]1[CH2:12][CH2:11][C:10]([NH:14][CH2:15][C:16]2[C:17](=[O:27])[N:18]([CH3:26])[C:19]3[C:24]([CH:25]=2)=[CH:23][CH:22]=[CH:21][CH:20]=3)([CH3:13])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[CH:37]1([C:43](Cl)=[O:44])[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]1>C(Cl)Cl>[CH2:1]([N:8]1[CH2:12][CH2:11][C:10]([N:14]([CH2:15][C:16]2[C:17](=[O:27])[N:18]([CH3:26])[C:19]3[C:24]([CH:25]=2)=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:43]([CH:37]2[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]2)=[O:44])([CH3:13])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 75938Cyclohexanecarbonyl chlorideHCID 81531DiisopropylethylamineHCID 584159153-{[(1-benzyl-3-methylpyrrolidin-3-yl)amino]methyl}-1-methylquinolin-2(1H)-one

Product 1

HCID 58415932N-(1-benzyl-3-methylpyrrolidin-3-yl)-N-[(1-methyl-2-oxo-1,2-dihydroquinolin-3-yl)methyl]cyclohexanecarboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 3-{[(1-benzyl-3-methylpyrrolidin-3-yl)amino]methyl}-1-methylquinolin-2(1H)-one (1846 mg, 5.11 mmol) in CH2Cl2 (25 ml) was added DIEA (1.338 ml, 7.66 mmol). Cyclohexane carbonyl chloride (0.757 ml, 5.62 mmol) was added and the reaction stirred for 2 hours. The reaction was quenched with MeOH then concentrated in vacuo. The resulting material was twice purified by silica gel chromatography on an Isco Companion (5-35% acetone/hexane for first run, 5-25% acetone/hexane for second run). 2.12 g, 88% over two steps.

Workup

  1. customThe reaction was quenched with MeOH
  2. concentrationthen concentrated in vacuo
  3. customThe resulting material was twice purified by silica gel chromatography on an Isco Companion (5-35% acetone/hexane for first run, 5-25% acetone/hexane for second run)

Sources & evidence

ORD record
ord-52068ab0d7c348218cbdbcd4ae6c3147
Source dataset
uspto-grants-2013_03
Patent number
US08389720B2

Reaction notes

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