Water → 4-Aza-spiro[2,5]octane-4-carboxylic acid N'-(5-fluoro-pyridin-2-yl)-hydrazide

HRID 2282708노트

반응식

HRID 2282708 반응식
[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][NH2:9])=[N:6][CH:7]=1.[CH2:10]1[C:12]2([CH2:17][CH2:16][CH2:15][CH2:14][N:13]2[C:18](Cl)=[O:19])[CH2:11]1.CCN(C(C)C)C(C)C.O>C(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][NH:9][C:18]([N:13]2[CH2:14][CH2:15][CH2:16][CH2:17][C:12]32[CH2:10][CH2:11]3)=[O:19])=[N:6][CH:7]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 199167865-Fluoro-2-hydrazinylpyridineHCID 866872634-Aza-spiro[2.5]octane-4-carbonyl chloride

생성물 1

HCID 866872644-Aza-spiro[2,5]octane-4-carboxylic acid N'-(5-fluoro-pyridin-2-yl)-hydrazide수율 74%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A red solution of (5-fluoro-pyridin-2-yl)-hydrazine (477 mg, 3.75 mmol), Intermediate 148a (3.00 mmol) and DIPEA (0.78 mL, 4.5 mmol) in DCM (20 mL) was stirred at reflux for 40 h. To the cooled solution was added water (20 mL) and the mixture shaken. The aqueous was extracted with DCM (2×10 mL), then the combined organics passed through a hydrophobic frit and concentrated in vacuo. Flash chromatography (silica 40 g, 1-5% [2M NH3 in MeOH] in DCM) gave the title compound as a yellow solid (587 mg, 74%). LCMS (Method 3): Rt 2.66 min, m/z 265 [MH+].

후처리

  1. temperatureat reflux for 40 h
  2. extractionThe aqueous was extracted with DCM (2×10 mL)
  3. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-d60cb855571e41e9ac7ce4bbfb99aa77
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09139584B2

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