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

HRID 2282708ノート

反応式

HRID 2282708 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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+].

後処理

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

出典と根拠

ORDレコード
ord-d60cb855571e41e9ac7ce4bbfb99aa77
出典データセット
uspto-grants-2015_09
特許番号
US09139584B2

反応ノート

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