HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Triethylamine → Methyl cis(+/-)-(4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-ethoxypiperidin-1-yl)(oxo)acetate

HRID 43719
Notes
Print preview

Reaction equation

HRID 43719 reaction equation
Cl.[Cl:2][C:3]1[N:4]=[C:5]([C:10]([NH:12][C@H:13]2[CH2:18][CH2:17][NH:16][CH2:15][C@H:14]2[O:19][CH2:20][CH3:21])=[O:11])[NH:6][C:7]=1[CH2:8][CH3:9].Cl[C:23](=[O:28])[C:24]([O:26][CH3:27])=[O:25].C(N(CC)CC)C>ClCCl.CN(C1C=CN=CC=1)C.C(OCC)(=O)C>[Cl:2][C:3]1[N:4]=[C:5]([C:10]([NH:12][C@H:13]2[CH2:18][CH2:17][N:16]([C:23](=[O:28])[C:24]([O:26][CH3:27])=[O:25])[CH2:15][C@H:14]2[O:19][CH2:20][CH3:21])=[O:11])[NH:6][C:7]=1[CH2:8][CH3:9]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 79846Methyl chloroglyoxylateHCID 86648665cis(+/-)-4-Chloro-N-(3-ethoxypiperidin-4-yl)-5-ethyl-1H-imidazole-2-carboxamide hydrochloride

Product 1

HCID 86648668Methyl cis(+/-)-(4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-ethoxypiperidin-1-yl)(oxo)acetateYield 90.7%

Reagents, catalysts & solvents 3

HCID 14284
4-(Dimethylamino)pyridine
Catalyst
HCID 6344DichloromethaneSolvent
HCID 8857Ethyl AcetateSolvent

Procedure

cis(±)-4-Chloro-N-(3-ethoxypiperidin-4-yl)-5-ethyl-1H-imidazole-2-carboxamide hydrochloride obtained in Example (131a) (200 mg, 0.593 mmol) was suspended in dichloromethane (5 mL). Methyl chloroglyoxylate (0.070 mL, 0.76 mmol), triethylamine (0.250 mL, 1.80 mmol) and DMAP (catalytic amount) were added under ice-cooling, and the mixture was stirred at room temperature for one hour. The reaction solution was diluted with ethyl acetate, washed with water and brine, and dried over anhydrous sodium sulfate. Following concentration under reduced pressure, the residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=7/3→1/0) to obtain 208.1 mg of the title compound as a colorless oily substance (91%).

Workup

  1. temperaturecooling
  2. washwashed with water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentration under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=7/3→1/0)

Sources & evidence

ORD record
ord-563fa248f14749d2b203dfb969b42586
Source dataset
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08536197B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes