Acetyl chloride → HCID 67171397, compound

HRID 551109Notes

Reaction equation

HRID 551109 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]([C:20]2[C:29]([OH:30])=[C:28]3[C:23]([CH:24]=[CH:25][CH:26]=[N:27]3)=[C:22]([Cl:31])[CH:21]=2)[NH:9][C:10](=[O:19])[CH2:11][O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:5]=[CH:6][CH:7]=1.CCN(C(C)C)C(C)C.[C:41](Cl)(=[O:43])[CH3:42]>C(Cl)Cl>[C:41]([NH:1][C:2]1[CH:3]=[C:4]([CH:8]([C:20]2[C:29]([OH:30])=[C:28]3[C:23]([CH:24]=[CH:25][CH:26]=[N:27]3)=[C:22]([Cl:31])[CH:21]=2)[NH:9][C:10](=[O:19])[CH2:11][O:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:5]=[CH:6][CH:7]=1)(=[O:43])[CH3:42]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 67172478HCID 67172478, compound

Product 1

HCID 67171397HCID 67171397, compoundYield 57.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the suspension of N-[(3-aminophenyl)(5-chloro-8-hydroxyquinolin-7-yl)methyl]-2-phenoxyacetamide (150 mg, 0.35 mmol) in methylenechloride (4 ml) cooled to 0 C was added DIEA (50 mg, 0.38 mmol) followed by acetylchloride (32.4 mg, 0.42 mmol). Purification by flush chromatography (eluent 30% acetone/DCM) afforded 96 mg (57%) of N-[[3-(acetylamino)phenyl](5-chloro-8-hydroxyquinolin-7-yl)methyl]-2-phenoxyacetamide as a white solid.

Workup

  1. temperaturecooled to 0 C
  2. customPurification
  3. customby flush chromatography (eluent 30% acetone/DCM)

Sources & evidence

ORD record
ord-a9faaeb269274c8ebdbf588e80a32512
Source dataset
uspto-grants-2011_05
Patent number
US07947712B2

Reaction notes

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