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

HRID 655776노트

반응식

HRID 655776 반응식
[Cl:1][C:2]1[C:3]([C:22]#[N:23])=[C:4]([C:8]([NH:10][C@@H:11]2[CH2:16][CH2:15][N:14](C(OC)=O)[CH2:13][C@@H:12]2[CH3:21])=[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:22]#[N:23])=[C:4]([C:8]([NH:10][C@@H:11]2[CH2:16][CH2:15][NH:14][CH2:13][C@@H:12]2[CH3:21])=[O:9])[NH:5][C:6]=1[CH3:7]

참가 물질

6

반응물 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 59402504methyl (3S,4R)-4-{[(4-chloro-3-cyano-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}-3-methylpiperidine-1-carboxylate2회

생성물 1

HCID 594026054-chloro-3-cyano-5-methyl-N-[(3S,4R)-3-methylpiperidin-4-yl]-1H-pyrrole-2-carboxamide수율 63.7%

시약·촉매·용매 1

HCID 174Ethylene Glycol용매

실험 절차

A solution of methyl (3S,4R)-4-{[(4-chloro-3-cyano-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}-3-methylpiperidine-1-carboxylate (Intermediate 42, 3.3 g, 8.39 mmol), potassium hydroxide (3.3 g, 58.77 mmol), and hydrazine hydrate (2.97 mL, 58.77 mmol) in ethylene glycol (200 mL) was stirred for 48 h at 120° C. The reaction mixture was poured in to water (200 mL), then extracted with ethyl acetate (2×250 mL). The combined organic layers were dried over anhydrous sodium sulphate, filtered, concentrated under vacuum to yield the crude product, which was triturated with water (100 mL) to afford 4-chloro-3-cyano-5-methyl-N-[(3S,4R)-3-methylpiperidin-4-yl]-1H-pyrrole-2-carboxamide 1.5 g (63%) as solid.

후처리

  1. extractionextracted with ethyl acetate (2×250 mL)
  2. dry with materialThe combined organic layers were dried over anhydrous sodium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum
  5. customto yield the crude product, which
  6. customwas triturated with water (100 mL)

출처 및 근거

ORD 기록
ord-ffdbe338d7014270a61c1d6ccc7b1935
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08071605B2

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