1,1'-Carbonyldiimidazole → HCID 68843504, compound

HRID 1725348Notes

Reaction equation

HRID 1725348 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:29]=[C:30]([F:32])[CH:31]=1)[O:5][CH2:6][CH2:7][N:8]([CH3:28])[CH2:9][CH2:10][CH2:11][NH:12][CH2:13][C@@H:14]([C:16]1[C:25]2[C:20](=[CH:21][CH:22]=[C:23]([O:26][CH3:27])[CH:24]=2)[N:19]=[CH:18][CH:17]=1)[OH:15].[C:33](N1C=CN=C1)(N1C=CN=C1)=[O:34]>C(Cl)Cl>[F:32][C:30]1[CH:29]=[C:4]([CH:3]=[C:2]([F:1])[CH:31]=1)[O:5][CH2:6][CH2:7][N:8]([CH3:28])[CH2:9][CH2:10][CH2:11][N:12]1[CH2:13][C@@H:14]([C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[C:23]([O:26][CH3:27])[CH:24]=3)[N:19]=[CH:18][CH:17]=2)[O:15][C:33]1=[O:34]

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 44535577(αR)-α-[[[3-[[2-(3,5-Difluorophenoxy)ethyl]methylamino]propyl]amino]methyl]-6-methoxy-4-quinolinemethanol

Product 1

HCID 68843504HCID 68843504, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of (R)-2-(3-{[2-(3,5-difluoro-phenoxy)-ethyl]-methyl-amino}-propylamino}-1-(6-methoxy-quinolin-4-yl)-ethanol (105 mg, 0.24 mmol), DMAP-(38 mg, 0.31 mmol), 1,1′-carbonyldiimidazole (51 mg, 0.31 mmol) and methylene chloride stabilised on amylene (4 ml) was stirred at room temperature for 16 hours. The solvent was concentrated and the residue was chromatographed on silicagel eluting with methylene chloride-methanol (94-6) to give (R)-3-(3-{[2-(3,5-difluoro-phenoxy)-ethyl]-methyl-amino)-propyl)-5-(6-methoxy-quinolin-4-yl)-oxazolidin-2-one (70 mg, 62%).

Workup

  1. concentrationThe solvent was concentrated
  2. customthe residue was chromatographed on silicagel
  3. washeluting with methylene chloride-methanol (94-6)

Sources & evidence

ORD record
ord-886f468c26714823bf32312429299622
Source dataset
uspto-grants-2009_02
Patent number
US07491714B2

Reaction notes

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