Sodium Hydroxide → 7-(4-Bromo-2-chlorophenylamino)-8-chloroimidazo[1,2-a]pyridine-6-carboxylic acid

HRID 494703ノート

反応式

HRID 494703 の反応式
[OH-].[Na+].C[O:4][C:5]([C:7]1[C:8]([NH:17][C:18]2[CH:23]=[CH:22][C:21]([Br:24])=[CH:20][C:19]=2[Cl:25])=[C:9]([Cl:16])[C:10]2[N:11]([CH:13]=[CH:14][N:15]=2)[CH:12]=1)=[O:6]>CO>[Br:24][C:21]1[CH:22]=[CH:23][C:18]([NH:17][C:8]2[C:7]([C:5]([OH:6])=[O:4])=[CH:12][N:11]3[CH:13]=[CH:14][N:15]=[C:10]3[C:9]=2[Cl:16])=[C:19]([Cl:25])[CH:20]=1

参加物

4

反応物 2

HCID 14798Sodium HydroxideHCID 58886653Methyl 7-(4-bromo-2-chlorophenylamino)-8-chloroimidazo[1,2-a]pyridine-6-carboxylate

生成物 1

HCID 115964897-(4-Bromo-2-chlorophenylamino)-8-chloroimidazo[1,2-a]pyridine-6-carboxylic acid

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

Sodium hydroxide (1.0 M aqueous solution, 14.6 mL, 14.6 mmol) was added to a solution of 7-(4-bromo-2-chlorophenylamino)-8-chloroimidazo[1,2-a]pyridine-6-carboxylic acid methyl ester (29) in methanol (30 mL) and the solution allowed to stir at room temperature overnight. Methanol was removed by rotary evaporation and the solution diluted with water and acidified to pH 2 by addition of 1.0 M HCl. The aqueous suspension was extracted with 4:1 ethyl acetate/THF. The organic extracts were washed with brine, dried over NaSO4, filtered, and concentrated in vacuo to provide the desired product as a light orange solid (30). MS (APCI+) m/z 400, 402, 404 (M+: Cl, Br pattern) detected. 1H NMR (400 MHz, methanol-d4) δ 9.01 (s, 1H), 7.83 (s, 1H), 7.51 (s, 2H), 7.25 (d, 1H), 6.60 (d, 1H).

後処理

  1. customMethanol was removed by rotary evaporation
  2. additionthe solution diluted with water
  3. additionacidified to pH 2 by addition of 1.0 M HCl
  4. extractionThe aqueous suspension was extracted with 4:1 ethyl acetate/THF
  5. washThe organic extracts were washed with brine
  6. dry with materialdried over NaSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-e515d23d7dc54464a5a51b184b041de1
出典データセット
uspto-grants-2009_05
特許番号
US07538120B2

反応ノート

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