Triethylamine → N-[2-chloro-4-({[3-(4-fluorophenyl)isoxazol-5-yl]methyl}amino)quinolin-3-yl]-2-ethoxyacetamide

HRID 606112Notes

Reaction equation

HRID 606112 reaction equation
[CH2:1]([O:3][CH2:4][C:5](Cl)=[O:6])[CH3:2].[Cl:8][C:9]1[C:18]([NH2:19])=[C:17]([NH:20][CH2:21][C:22]2[O:26][N:25]=[C:24]([C:27]3[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=3)[CH:23]=2)[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=1.C(N(CC)CC)C>ClCCl>[Cl:8][C:9]1[C:18]([NH:19][C:5](=[O:6])[CH2:4][O:3][CH2:1][CH3:2])=[C:17]([NH:20][CH2:21][C:22]2[O:26][N:25]=[C:24]([C:27]3[CH:28]=[CH:29][C:30]([F:33])=[CH:31][CH:32]=3)[CH:23]=2)[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 84189Ethoxyacetyl chloride3×HCID 866168902-chloro-N4-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}quinoline-3,4-diamine

Product 1

HCID 86616894N-[2-chloro-4-({[3-(4-fluorophenyl)isoxazol-5-yl]methyl}amino)quinolin-3-yl]-2-ethoxyacetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under a nitrogen atmosphere, ethoxyacetyl chloride (5.5 g, 45 mmol) was added dropwise to a solution of 2-chloro-N4-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}quinoline-3,4-diamine (15.00 g, 40.67 mmol) and triethylamine (8.5 mL, 61 mmol) in dichloromethane (200 mL) at 6° C. After the reaction was stirred for 30 minutes, an analysis by HPLC indicated the presence of starting material, and additional ethoxyacetyl chloride (1.01 g) was added. The stirring was continued, and over the course of five hours, a total of 13 g of ethoxyacetyl chloride was added. The work-up procedure described in Part A of Example 19 was followed to provide N-[2-chloro-4-({[3-(4-fluorophenyl)isoxazol-5-yl]methyl}amino)quinolin-3-yl]-2-ethoxyacetamide as an orange solid.

Workup

  1. additionwas added

Sources & evidence

ORD record
ord-ddc4a474448a4120a626be37f3769012
Source dataset
uspto-grants-2011_03
Patent number
US07915281B2

Reaction notes

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