Hydrazine hydrate (1:1) → HCID 178527570, compound

HRID 456640Notes

Reaction equation

HRID 456640 reaction equation
[N:1]1([CH2:7][CH2:8][NH:9][S:10]([C:13]2[CH:17]=[C:16]([C:18]([C:20]3[C:21](Cl)=[N:22][CH:23]=[CH:24][CH:25]=3)=O)[NH:15][CH:14]=2)(=[O:12])=[O:11])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.O.[NH2:28][NH2:29]>C(O)C>[N:1]1([CH2:7][CH2:8][NH:9][S:10]([C:13]2[CH:17]=[C:16]([C:18]3[C:20]4[C:21](=[N:22][CH:23]=[CH:24][CH:25]=4)[NH:29][N:28]=3)[NH:15][CH:14]=2)(=[O:12])=[O:11])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 865922425-(2-chloro-pyridine-3-carbonyl)-1H-pyrrole-3-sulfonic acid (2-morpholin-4-yl-ethyl)-amide

Product 1

HCID 178527570HCID 178527570, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 5-(2-chloro-pyridine-3-carbonyl)-1H-pyrrole-3-sulfonic acid (2-morpholin-4-yl-ethyl)-amide (100 mg) and hydrazine hydrate (excess) in ethanol (5 mL) was heated at 80° C. for 48 hours. The reaction was concentrated, diluted with water, acidified to pH 2 with 1N HCl and extracted with DCM. The aqueous layer was adjusted to pH 7 with NaHCO3, the precipitate was collected by vacuum filtration, washed with water to give the titled compound as a white solid.

Workup

  1. concentrationThe reaction was concentrated
  2. additiondiluted with water
  3. extractionextracted with DCM
  4. filtrationthe precipitate was collected by vacuum filtration
  5. washwashed with water

Sources & evidence

ORD record
ord-16be027b9a7f49a3834919ba6088bf30
Source dataset
uspto-grants-2007_03
Patent number
US07186716B2

Reaction notes

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