Dimethylamine → HCID 67172140, compound

HRID 551111Notes

Reaction equation

HRID 551111 reaction equation
Cl[CH2:2][C:3]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH:12]([C:24]2[C:33]([OH:34])=[C:32]3[C:27]([CH:28]=[CH:29][CH:30]=[N:31]3)=[C:26]([Cl:35])[CH:25]=2)[NH:13][C:14](=[O:23])[CH2:15][O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:7]=1)=[O:4].[CH3:36][NH:37][CH3:38]>>[Cl:35][C:26]1[CH:25]=[C:24]([CH:12]([NH:13][C:14](=[O:23])[CH2:15][O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:8]2[CH:7]=[C:6]([NH:5][C:3](=[O:4])[CH2:2][N:37]([CH3:38])[CH3:36])[CH:11]=[CH:10][CH:9]=2)[C:33]([OH:34])=[C:32]2[C:27]=1[CH:28]=[CH:29][CH:30]=[N:31]2

Participants

3

Reactant 2

HCID 674DimethylamineHCID 67172242HCID 67172242, compound

Product 1

HCID 67172140HCID 67172140, compoundYield 46%

Procedure

A solution of 2-chloro-N-(3-{(5-chloro-8-hydroxyquinolin-7-yl)[(phenoxyacetyl)amino]methyl}phenyl)acetamide (100 mg, 0.20 mmol) and dimethylamine (2M/THF, 10 eq.) was heated at 45 C for 18 h. The solvent was removed in vacuo, the residue was dissolved in methylene chloride and washed with water and brine. The organic layer was dried over sodium sulfate and concentrated in vacuo to afford 48 mg (46%) of N-(3-{(5-chloro-8-hydroxyquinolin-7-yl)[(phenoxyacetyl)amino]methyl}phenyl)-N2,N2-dimethylglycinamide as a beige solid.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in methylene chloride
  3. washwashed with water and brine
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0316bc83f432495982612a7e0f90354e
Source dataset
uspto-grants-2011_05
Patent number
US07947712B2

Reaction notes

Loading…