4-Methylthiazole → 3-{3-[4-(3-Chloro-4-fluoro-phenylamino)-3-cyano-7-methoxy-quinolin-6-ylcarbamoyl]-allyl}-4-methyl-thiazol-3-ium bromide

HRID 379170Notes

Reaction equation

HRID 379170 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([O:27][CH3:28])=[C:17]([NH:20][C:21](=[O:26])[CH:22]=[CH:23][CH2:24][Br:25])[CH:18]=3)[N:13]=[CH:12][C:11]=2[C:29]#[N:30])[CH:5]=[CH:6][C:7]=1[F:8].[CH3:31][C:32]1[N:33]=[CH:34][S:35][CH:36]=1>C(OCC)(=O)C>[Br-:25].[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([O:27][CH3:28])=[C:17]([NH:20][C:21]([CH:22]=[CH:23][CH2:24][N+:33]4[C:32]([CH3:31])=[CH:36][S:35][CH:34]=4)=[O:26])[CH:18]=3)[N:13]=[CH:12][C:11]=2[C:29]#[N:30])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

4

Reactant 2

HCID 127484-MethylthiazoleHCID 542420754-Bromo-but-2-enoic acid[4-(3-chloro-4-fluoro-phenylamino)-3-cyano-7-methoxy-quinolin-6-yl]-amide

Product 1

HCID 672018203-{3-[4-(3-Chloro-4-fluoro-phenylamino)-3-cyano-7-methoxy-quinolin-6-ylcarbamoyl]-allyl}-4-methyl-thiazol-3-ium bromideYield 36.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 0.7 g (1.4 mmol) of 4-bromo-but-2-enoic acid[4-(3-chloro-4-fluoro-phenylamino)-3-cyano-7-methoxy-quinolin-6-yl]-amide and 0.85 g (8.6 mmol) of 4-methyl thiazole was refluxed for 17 hr. The mixture was diluted with ethyl acetate and cooled. Solid was collected and recrystallized from methanol-acetone-ethyl acetate to give 0.3 g of the title compound as a yellow powder: mass spectrum (electrospray, m/e): M+507.9, 509.8, (M+H)+22254.4, 255.1.

Workup

  1. temperaturecooled
  2. customSolid was collected
  3. customrecrystallized from methanol-acetone-ethyl acetate

Sources & evidence

ORD record
ord-b4e30d59fc1b4d169e97ef10f1c8ee45
Source dataset
uspto-grants-2001_10
Patent number
US06297258B1

Reaction notes

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