Chloroacetyl chloride → HCID 67172242, compound

HRID 551110Notes

Reaction equation

HRID 551110 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.[Cl:41][CH2:42][C:43](Cl)=[O:44]>C(Cl)Cl>[Cl:41][CH2:42][C:43]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[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:3]=1)=[O:44]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 81531DiisopropylethylamineHCID 67172478HCID 67172478, compound

Product 1

HCID 67172242HCID 67172242, compoundYield 53.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of N-[(3-aminophenyl)(5-chloro-8-hydroxyquinolin-7-yl)methyl]-2-phenoxyacetamide (800 mg, 1.84 mmol) in methylenechloride (30 ml) cooled to 0 C was added DIEA (300 mg, 2.32 mmol) followed by chloroacetyl chloride (300 mg, 2.65 mmol). Purification by flush chromatography (eluent 30% acetone/DCM) afforded 500 mg (53%) of 2-chloro-N-(3-{(5-chloro-8-hydroxyquinolin-7-yl)[(phenoxyacetyl)amino]methyl}phenyl)acetamide an off-white solid.

Workup

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

Sources & evidence

ORD record
ord-09ead0feb86b4f0a8b8bc0b6081613b7
Source dataset
uspto-grants-2011_05
Patent number
US07947712B2

Reaction notes

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