Lithium hydroxide, monohydrate → 5-Cyclopropyl-6-(2,4-dichloro-phenylamino)-pyridine-2-carboxylic acid

HRID 927338

반응식

HRID 927338 반응식
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]2[CH2:13][CH2:12]2)=[C:7]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=2[Cl:22])[N:6]=1)=[O:4].O.[OH-].[Li+]>C1COCC1.O>[CH:11]1([C:8]2[CH:9]=[CH:10][C:5]([C:3]([OH:4])=[O:2])=[N:6][C:7]=2[NH:14][C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=2[Cl:22])[CH2:12][CH2:13]1

참가 물질

5

반응물 2

HCID 168937Lithium hydroxide, monohydrateHCID 710873965-Cyclopropyl-6-(2,4-dichloro-phenylamino)-pyridine-2-carboxylic acid methyl ester

생성물 1

HCID 710872815-Cyclopropyl-6-(2,4-dichloro-phenylamino)-pyridine-2-carboxylic acid수율 10.1%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

A solution of 5-cyclopropyl-6-(2,4-dichloro-phenylamino)-pyridine-2-carboxylic acid methyl ester (62 mg, 184 μmol) and lithium hydroxide hydrate (9.3 mg, 221 μmol) in THF (100 μl) and water (50 μl) was stirred at ambient temperature for 20 h. The reaction mixture was poured onto 1 M HCl/ice water (1×20 mL) and extracted with i-PrOAc (2×25 mL). The combined organic layers were dried over sodium sulfate. The solvent was removed under reduced pressure to obtain the title compound (6 mg, 10%) as colorless liquid, which was sufficiently pure to be used in the next reaction step, MS (EI): m/e=323.3 [M+H]+.

후처리

  1. extractionextracted with i-PrOAc (2×25 mL)
  2. dry with materialThe combined organic layers were dried over sodium sulfate
  3. customThe solvent was removed under reduced pressure

출처 및 근거

ORD 기록
ord-23c1b1f9ebd6476094bd51c7c3cc5c7a
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09290451B2

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