Water → 4-chloro-3-cyano-N-[(3S,4R)-3-ethoxypiperidin-4-yl]-5-methyl-1H-pyrrole-2-carboxamide

HRID 655767ノート

反応式

HRID 655767 の反応式
[Cl:1][C:2]1[C:3]([C:25]#[N:26])=[C:4]([C:8]([NH:10][C@@H:11]2[CH2:16][CH2:15][N:14](C(OCC)=O)[CH2:13][C@@H:12]2[O:22][CH2:23][CH3:24])=[O:9])[NH:5][C:6]=1[CH3:7].[OH-].[K+].O.NN.O>C(O)CO>[Cl:1][C:2]1[C:3]([C:25]#[N:26])=[C:4]([C:8]([NH:10][C@@H:11]2[CH2:16][CH2:15][NH:14][CH2:13][C@@H:12]2[O:22][CH2:23][CH3:24])=[O:9])[NH:5][C:6]=1[CH3:7]

参加物

6

反応物 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 59402508ethyl (3S,4R)-4-{[(4-chloro-3-cyano-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}-3-ethoxypiperidine-1-carboxylate2 回

生成物 1

HCID 594024474-chloro-3-cyano-N-[(3S,4R)-3-ethoxypiperidin-4-yl]-5-methyl-1H-pyrrole-2-carboxamide収率 55%

試薬・触媒・溶媒 1

HCID 174Ethylene Glycol溶媒

実験手順

A solution of ethyl (3S,4R)-4-{[(4-chloro-3-cyano-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}-3-ethoxypiperidine-1-carboxylate (Intermediate 32, 1.5 g, 3.92 mmol), potassium hydroxide (1.54 g, 27.48 mmol), and hydrazine hydrate (1.38 mL, 27.48 mmol) in ethylene glycol (200 mL) was stirred for 60 h at 120° C. The reaction mixture was poured in to water (300 mL) and extracted with ethyl acetate (2×300 mL). The combined organic extracts were dried over anhydrous sodium sulphate, filtered, concentrated under vacuum to yield the crude product which was triturated with water (150 mL) to afford 4-chloro-3-cyano-N-[(3S,4R)-3-ethoxypiperidin-4-yl]-5-methyl-1H-pyrrole-2-carboxamide (670 mg, 55%) as solid.

後処理

  1. extractionextracted with ethyl acetate (2×300 mL)
  2. dry with materialThe combined organic extracts were dried over anhydrous sodium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum
  5. customto yield the crude product which
  6. customwas triturated with water (150 mL)

出典と根拠

ORDレコード
ord-3302917e9ba04293833ead4aa176d621
出典データセット
uspto-grants-2011_12
特許番号
US08071605B2

反応ノート

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