Methoxyacetyl chloride → N-{4-[(2-hydroxy-2-methylpropyl)amino]quinolin-3-yl}-2-methoxyacetamide hydrochloride

HRID 547330Notes

Reaction equation

HRID 547330 reaction equation
[CH3:1][O:2][CH2:3][C:4]([Cl:6])=[O:5].[NH2:7][C:8]1[CH:9]=[N:10][C:11]2[C:16]([C:17]=1[NH:18][CH2:19][C:20]([CH3:23])([OH:22])[CH3:21])=[CH:15][CH:14]=[CH:13][CH:12]=2>C(#N)C>[ClH:6].[OH:22][C:20]([CH3:23])([CH3:21])[CH2:19][NH:18][C:17]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=[CH:9][C:8]=1[NH:7][C:4](=[O:5])[CH2:3][O:2][CH3:1]

Participants

4

Reactant 2

HCID 96623Methoxyacetyl chlorideHCID 149869411-((3-Aminoquinolin-4-yl)amino)-2-methylpropan-2-ol

Product 1

HCID 67204879N-{4-[(2-hydroxy-2-methylpropyl)amino]quinolin-3-yl}-2-methoxyacetamide hydrochloride

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Methoxyacetyl chloride (2.5 g, 23 mmol) was added dropwise to a solution of 1-[(3-aminoquinolin-4-yl)amino]-2-methylpropan-2-ol (prepared as described in Part A of Example 8, approximately 4.4 g, 19 mmol) in acetonitrile (96 mL). The reaction mixture was stirred for 1 hour at room temperature. A solid formed that was isolated by filtration, washed with acetonitrile, and dried to yield 5.5 g of N-{4-[(2-hydroxy-2-methylpropyl)amino]quinolin-3-yl}-2-methoxyacetamide hydrochloride as a yellow powder.

Workup

  1. customprepared
  2. customA solid formed that
  3. customwas isolated by filtration
  4. washwashed with acetonitrile
  5. customdried

Sources & evidence

ORD record
ord-98aef4e1d4c6423f8d5420b071aef5ab
Source dataset
uspto-grants-2011_05
Patent number
US07939526B2

Reaction notes

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