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

HRID 1766792노트

반응식

HRID 1766792 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-49856dc55af5461f92838e009b413e7d
출처 데이터셋
uspto-grants-2007_06
특허 번호
US07230099B2

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