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

HRID 655774Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 655774
[Cl:1][C:2]1[C:6]([Cl:7])=[C:5]([CH3:8])[NH:4][C:3]=1[C:9]([NH:11][C@@H:12]1[CH2:17][CH2:16][N:15](C(OC)=O)[CH2:14][C@@H:13]1[CH3:22])=[O:10].[OH-].[K+].O.NN.O>C(O)CO>[Cl:1][C:2]1[C:6]([Cl:7])=[C:5]([CH3:8])[NH:4][C:3]=1[C:9]([NH:11][C@@H:12]1[CH2:17][CH2:16][NH:15][CH2:14][C@@H:13]1[CH3:22])=[O:10]

Komponenten

6

Edukt 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 59402510methyl (3S,4R)-4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}-3-methylpiperidine-1-carboxylate2×

Produkt 1

HCID 594024943,4-dichloro-5-methyl-N-[(3S,4R)-3-methylpiperidin-4-yl]-1H-pyrrole-2-carboxamideAusbeute 63,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 174Ethylene GlycolLösungsmittel

Versuchsvorschrift

A solution of methyl (3S,4R)-4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}-3-methylpiperidine-1-carboxylate (Intermediate 40, 3.4 g, 9.79 mmol), potassium hydroxide (3.84 g, 68.58 mmol), and hydrazine hydrate (3.6 mL, 68.58 mmol) in ethylene glycol (180 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 3,4-dichloro-5-methyl-N-[(3S,4R)-3-methylpiperidin-4-yl]-1H-pyrrole-2-carboxamide 1.8 g, (63%) as solid.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-9a232bc7258440e3b549e269849ab5b1
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08071605B2

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