Ethoxyacetyl chloride → N-[7-bromo-4-(2-hydroxy-2-methylpropylamino)quinolin-3-yl]-2-ethoxyacetamide

HRID 9380

Reaction equation

HRID 9380 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[NH:12][CH2:13][C:14]([CH3:17])([OH:16])[CH3:15])=[CH:9][CH:8]=[C:7]([Br:18])[CH:6]=2.[CH2:19]([O:21][CH2:22][C:23](Cl)=[O:24])[CH3:20]>ClCCl>[Br:18][C:7]1[CH:6]=[C:5]2[C:10]([C:11]([NH:12][CH2:13][C:14]([OH:16])([CH3:15])[CH3:17])=[C:2]([NH:1][C:23](=[O:24])[CH2:22][O:21][CH2:19][CH3:20])[CH:3]=[N:4]2)=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 84189Ethoxyacetyl chlorideHCID 219844571-(3-Amino-7-bromoquinolin-4-ylamino)-2-methylpropan-2-ol

Product 1

HCID 21984424N-[7-bromo-4-(2-hydroxy-2-methylpropylamino)quinolin-3-yl]-2-ethoxyacetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1-(3-amino-7-bromoquinolin-4-ylamino)-2-methylpropan-2-ol (158.19 g, 0.510 mol) in dichloromethane (1.2 L) was cooled to 0° C. Ethoxyacetyl chloride (62.50 g, 0.510 mol) was added dropwise, and then the reaction was allowed to warm to ambient temperature and stirred overnight. A precipitate formed and was isolated by filtration to provide N-[7-bromo-4-(2-hydroxy-2-methylpropylamino)quinolin-3-yl]-2-ethoxyacetamide as a solid.

Workup

  1. customA precipitate formed
  2. customwas isolated by filtration

Sources & evidence

ORD record
ord-408b6bd98e6c455a89225c1e8c5e9238
Source dataset
uspto-grants-2006_08
Patent number
US07091214B2

Linked notes

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