Triethylamine → HCID 86616897, compound

HRID 606119Notes

Reaction equation

HRID 606119 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][CH2:22][C:23]2[O:27][N:26]=[C:25]([C:28]3[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=3)[CH:24]=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][CH2:22][C:23]2[O:27][N:26]=[C:25]([C:28]3[CH:29]=[CH:30][C:31]([F:34])=[CH:32][CH:33]=3)[CH:24]=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 86616896HCID 86616896, compound

Product 1

HCID 86616897HCID 86616897, compoundYield 100.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under a nitrogen atmosphere, ethoxyacetyl chloride (3.5 g, 28 mmol) was added dropwise to a solution of 2-chloro-N4-{2-[3-(4-fluorophenyl)isoxazol-5-yl]ethyl}quinoline-3,4-diamine (9.0 g, 23.5 mmol) and anhydrous triethylamine (10.0 mL, 35.3 mmol) in anhydrous dichloromethane (75 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 (2.0 g) was added. After the reaction was stirred for another 30 minutes, it was still incomplete, and additional ethoxyacetyl chloride (2.0 g) was added. The stirring was continued for an additional 30 minutes, and the work-up procedure described in Part A of Example 19 was followed to provide 11.12 g of N-[2-chloro-4-({2-[3-(4-fluorophenyl)isoxazol-5-yl]ethyl}amino)quinolin-3-yl]-2-ethoxyacetamide as a white solid.

Workup

  1. additionwas added
  2. stirringAfter the reaction was stirred for another 30 minutes
  3. waitThe stirring was continued for an additional 30 minutes

Sources & evidence

ORD record
ord-bbdfc3e73c154f0c9d5b9c6545288094
Source dataset
uspto-grants-2011_03
Patent number
US07915281B2

Reaction notes

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