Water → (S)-2-Methyl-piperidine-1-carboxylic acid N'-(5-fluoro-pyridin-2-yl)-hydrazide

HRID 630819ノート

反応式

HRID 630819 の反応式
[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][NH2:9])=[N:6][CH:7]=1.CCN(C(C)C)C(C)C.[CH3:19][C@H:20]1[CH2:25][CH2:24][CH2:23][CH2:22][N:21]1[C:26](Cl)=[O:27].O>C(Cl)Cl.CO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][NH:9][C:26]([N:21]2[CH2:22][CH2:23][CH2:24][CH2:25][C@@H:20]2[CH3:19])=[O:27])=[N:6][CH:7]=1

参加物

7

反応物 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 199167865-Fluoro-2-hydrazinylpyridineHCID 45081356(2S)-2-Methylpiperidine-1-carbonyl chloride

生成物 1

HCID 86687104(S)-2-Methyl-piperidine-1-carboxylic acid N'-(5-fluoro-pyridin-2-yl)-hydrazide収率 57%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of (5-fluoro-pyridin-2-yl)-hydrazine (582 mg, 4.58 mmol) and DIPEA (0.997 mL, 5.72 mmol) in dry DCM (20 mL) was added Intermediate 81a (740 mg, 4.58 mmol) and the resulting red solution stirred at RT for 66 h, and at reflux for 4 h. To the cooled solution was added water (20 mL) and the mixture shaken. The aqueous was extracted with DCM (20 mL), then the combined organics passed through a hydrophobic frit and concentrated in vacuo to leave a pale brown solid. FCC, using 0-5% MeOH in DCM, gave the title compound as a pale yellow solid (657 mg, 57%). 1H NMR (300 MHz, CDCl3): 1.22 (3H, d, J 6.9), 1.40-1.77 (6H, m), 2.96 (1H, td, J 13.0, 2.9), 3.85 (1H, ddd, J 13.3, 4.5, 2.2), 4.31 (1H, m), 6.50 (1H, s), 6.59 (1H, br s), 6.75 (1H, ddd, J 9.0, 3.6, 0.7), 7.27 (1H, ddd, J 9.1, 8.1, 3.1), 8.02 (1H, d, J 2.9).

後処理

  1. temperatureat reflux for 4 h
  2. stirringthe mixture shaken
  3. extractionThe aqueous was extracted with DCM (20 mL)
  4. concentrationconcentrated in vacuo
  5. customto leave a pale brown solid

出典と根拠

ORDレコード
ord-4303def3c6c54618bf7018c6c48ec0df
出典データセット
uspto-grants-2016_04
特許番号
US09315503B2

反応ノート

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