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Water → TAK-603

HRID 964587
Notes
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Reaction equation

HRID 964587 reaction equation
[H-].[Na+].[NH:3]1[CH:7]=[N:6][CH:5]=[N:4]1.[CH2:8]([O:10][C:11]([C:13]1[C:14]([CH2:37]Cl)=[N:15][C:16]2[C:21]([C:22]=1[C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[C:25]([O:31][CH3:32])[CH:24]=1)=[CH:20][C:19]([O:33][CH3:34])=[C:18]([O:35][CH3:36])[CH:17]=2)=[O:12])[CH3:9].O>CN(C)C=O>[CH2:8]([O:10][C:11]([C:13]1[C:14]([CH2:37][N:3]2[CH:7]=[N:6][CH:5]=[N:4]2)=[N:15][C:16]2[C:21]([C:22]=1[C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[C:25]([O:31][CH3:32])[CH:24]=1)=[CH:20][C:19]([O:33][CH3:34])=[C:18]([O:35][CH3:36])[CH:17]=2)=[O:12])[CH3:9]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 92571H-1,2,4-TriazoleHCID 24758Sodium hydrideHCID 10813243Ethyl 2-chloromethyl-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinoline-3-carboxylate

Product 1

HCID 153980TAK-603Yield 53%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

Oily sodium hydride (60%,0.323 g) was added to a solution of 1H-1,2,4-triazole (0.558 g) in N,N-dimethylformamide (30 ml), followed by stirring at room temperature for 15 minutes. Then 2-chloromethyl-6,7-dimethoxy-4-(3,4-dimethoxyphenyl)quinoline-3-carboxylic acid ethyl ester (3.0 g) was added. After stirring at 80° C. for 1 hour, the reaction mixture was poured over water and extracted with ethyl acetate. The ethyl acetate layer was washed with water and then dried (MgSO4), after which the solvent was distilled off. The residue was subjected to silica gel column chromatography and eluted with chloroform-methanol (40:1, v/v) to yield 6,7-dimethoxy-4-(3,4-dimethoxyphenyl)-2-(1,2,4-triazol-1-ylmethyl)quinoline-3-carboxylic acid ethyl ester (1.7 g, 53%), which was then recrystallized from ethyl acetate-hexane to yield a colorless prismatic crystal having a melting point of 176° to 177° C.

Workup

  1. stirringAfter stirring at 80° C. for 1 hour
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with water
  4. dry with materialdried (MgSO4)
  5. distillationafter which the solvent was distilled off
  6. washeluted with chloroform-methanol (40:1

Sources & evidence

ORD record
ord-3d4f841351644197965ffeaae320eec4
Source dataset
uspto-grants-1998_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05770602

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes