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

HRID 655774Notes

Reaction equation

HRID 655774 reaction equation
[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]

Participants

6

Reactant 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×

Product 1

HCID 594024943,4-dichloro-5-methyl-N-[(3S,4R)-3-methylpiperidin-4-yl]-1H-pyrrole-2-carboxamideYield 63.4%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

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.

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
  5. customto yield the crude product, which
  6. customwas triturated with water (150 mL)

Sources & evidence

ORD record
ord-9a232bc7258440e3b549e269849ab5b1
Source dataset
uspto-grants-2011_12
Patent number
US08071605B2

Reaction notes

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