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

HRID 655785Notes

Reaction equation

HRID 655785 reaction equation
[Cl:1][C:2]1[CH:3]=[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][CH2:24][CH3:25])=[O:9])[NH:5][C:6]=1[CH3:7].[OH-].[K+].O.NN.O>C(O)CO>[Cl:1][C:2]1[CH:3]=[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][CH2:24][CH3:25])=[O:9])[NH:5][C:6]=1[CH3:7]

Participants

6

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 66707582ethyl (3R,4S)-4-{[(4-chloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}-3-propoxypiperidine-1-carboxylate2×

Product 1

HCID 594024424-chloro-5-methyl-N-[(3S,4R)-3-propoxypiperidin-4-yl]-1H-pyrrole-2-carboxamideYield 30%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

A solution of ethyl (3R,4S)-4-{[(4-chloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}-3-propoxypiperidine-1-carboxylate (Intermediate 73, 2.8 g, 7.547 mmol) potassium hydroxide (4.2 g, 75.47 mmol), and Hydrazine hydrate (3.6 mL, 75.47 mmol) in ethylene glycol (100 mL) was stirred for 60 h at 120° C. The reaction mixture was poured into water (300 mL) and extracted with ethyl acetate (2×300 mL). The combined organic extracts were dried over anhydrous sodium sulphate, filtered, and concentrated under vacuum to afford 4-chloro-5-methyl-N-[(3S,4R)-3-propoxypiperidin-4-yl]-1H-pyrrole-2-carboxamide 650 mg, 30% as solid.

Workup

  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

Sources & evidence

ORD record
ord-8df58f6183694e81aaee182614a72627
Source dataset
uspto-grants-2011_12
Patent number
US08071605B2

Reaction notes

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