2-Chloroethanol → HCID 21925549, compound

HRID 2118050Notes

Reaction equation

HRID 2118050 reaction equation
C([N:4](CC)C(C)C)(C)C.Cl[CH2:11][CH2:12][OH:13].[Cl:14][C:15]1[CH:40]=[CH:39][C:18]2[N:19]3[C:23]([CH2:24][NH:25][CH2:26][C:17]=2[CH:16]=1)=[N:22][N:21]=[C:20]3[CH:27]1[CH2:32][CH2:31][N:30]([C:33]2[N:38]=[CH:37][CH:36]=[CH:35][N:34]=2)[CH2:29][CH2:28]1>CN(C)C=O>[NH3:4].[Cl:14][C:15]1[CH:40]=[CH:39][C:18]2[N:19]3[C:23]([CH2:24][N:25]([CH2:11][CH2:12][OH:13])[CH2:26][C:17]=2[CH:16]=1)=[N:22][N:21]=[C:20]3[CH:27]1[CH2:32][CH2:31][N:30]([C:33]2[N:34]=[CH:35][CH:36]=[CH:37][N:38]=2)[CH2:29][CH2:28]1

Participants

6

Reactant 3

HCID 342-ChloroethanolHCID 81531DiisopropylethylamineHCID 21925629HCID 21925629, compound

Product 2

HCID 222AmmoniaHCID 21925549HCID 21925549, compoundYield 54.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N,N-Diisopropylethylamine (80 μl, 0.62 mmol), followed by 2-chloroethanol (52 μl, 0.78 mmol) were added to a solution of the amine from example 12 (200 mg, 0.52 mmol) in N,N-dimethylformamide (6 ml), and the reaction mixture was stirred at room temperature for 18 hours. The mixture was concentrated under reduced pressure and the residue was purified by column chromatography on silica gel using ethyl acetate:methanol:0.88 ammonia (90:10:1) as eluant, to give the title compound as an off-white solid (120 mg).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customthe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-5e2bb7dd56394833ab135f77545676ed
Source dataset
uspto-grants-2008_10
Patent number
US07442795B2

Reaction notes

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