Triethylamine → HCID 57550247, compound

HRID 548642Notes

Reaction equation

HRID 548642 reaction equation
C(N(CC)CC)C.[CH:8]1([C:11]([OH:13])=O)[CH2:10][CH2:9]1.[CH:14]1([CH2:20][NH:21][CH2:22][C@H:23]2[N:27]([C:28]3[CH:33]=[CH:32][C:31]([O:34][CH2:35][CH2:36][CH2:37][N:38]4[CH2:42][CH2:41][CH2:40][CH:39]4[CH3:43])=[CH:30][CH:29]=3)[C:26](=[O:44])[CH2:25][CH2:24]2)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>ClCCl>[CH:14]1([CH2:20][N:21]([CH2:22][C@@H:23]2[CH2:24][CH2:25][C:26](=[O:44])[N:27]2[C:28]2[CH:33]=[CH:32][C:31]([O:34][CH2:35][CH2:36][CH2:37][N:38]3[CH2:42][CH2:41][CH2:40][CH:39]3[CH3:43])=[CH:30][CH:29]=2)[C:11]([CH:8]2[CH2:10][CH2:9]2)=[O:13])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 15655Cyclopropanecarboxylic acidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 16663102HCID 16663102, compound

Product 1

HCID 57550247HCID 57550247, compoundYield 105.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (0.13 ml, 0.93 mmol, 2 eq) is added to a solution of cyclopropanecarboxylic acid (40 mg, 0.47 mmol, 1 eq) and ((5S)-5-{[(cyclohexylmethyl)amino]methyl}-1-{4-[3-(2-methylpyrrolidin-1-yl)propoxy]phenyl}pyrrolidin-2-one 1 (200 mg, 0.47 mmol, 1 eq) in dichloromethane (5 ml). The mixture is cooled with an ice bath. 1-Hydroxybenzotriazole (12 mg, 0.093 mmol, 0.2 eq), and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (99 mg, 0.52 mmol, 1.1 eq) are added. The mixture is stirred at room temperature for 5 hours, washed with water and brine, dried over magnesium sulfate and concentrated in vacuo to give 0.246 g of yellow oil that is purified by chromatography over silicagel (dichloromethane/methanol/ammonia 96/4/0.4) to afford 0.135 g of N-(cyclohexylmethyl)-N-[((2S)-1-{4-[3-(2-methylpyrrolidin-1-yl)propoxy]phenyl}-5-oxopyrrolidin-2-yl)methyl]cyclopropanecarboxamide 77 as a yellow lacquer.

Workup

  1. temperatureThe mixture is cooled with an ice bath
  2. washwashed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9a2076f67af041ad9849c73aabff18f0
Source dataset
uspto-grants-2011_05
Patent number
US07943605B2

Reaction notes

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