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Methanol → 2-[3-(Phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-1-yl]ethylamine dihydrochloride

HRID 2416751
Notes
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Reaction equation

HRID 2416751 reaction equation
[C:1]1([S:7]([C:10]2[C:18]3[C:13](=[N:14][CH:15]=[CH:16][CH:17]=3)[N:12]([CH2:19][CH2:20][N:21]3C(=O)C4C(=CC=CC=4)C3=O)[CH:11]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.NN.CO.C(Cl)[Cl:37]>O1CCOCC1>[ClH:37].[ClH:37].[C:1]1([S:7]([C:10]2[C:18]3[C:13](=[N:14][CH:15]=[CH:16][CH:17]=3)[N:12]([CH2:19][CH2:20][NH2:21])[CH:11]=2)(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 887MethanolHCID 6344DichloromethaneHCID 9321HydrazineHCID 220281762-{2-[3-(Phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine-1-yl]ethyl}-1H-isoindole-1,3(2H)-dione

Product 1

HCID 220281972-[3-(Phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-1-yl]ethylamine dihydrochloride

Reagents, catalysts & solvents 1

HCID 31275
1,4-Dioxane
Solvent

Conditions

Temperature
50 °C

Procedure

A solution of 2-{2-[3-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-1-yl]ethyl}-1H-isoindole-1,3(2H)-dione (4.54 g, 10.5 mmol) in dioxane is treated with anhydrous hydrazine (8.3 mL, 265 mmol), heated at 50° C. for 3 h, concentrated in vacuo, diluted with water and extracted with CH2Cl2. The combined extracts are dried over MgSO4 and concentrated in vacuo to give a clear gum residue. Chromatography (1:9 methanol:CH2Cl2) of the residue affords the free amine of the title compound as a clear gum. The free amine is dissolved in ethanol, acidified with 2N aqueous HCl and concentration in vacuo. Crystallization of the resultant residue from ethanol/ether affords the title compound as a white solid, 3.20 g, mp 195-197° C., characterized by mass spectral and HNMR analyses.

Workup

  1. concentrationconcentrated in vacuo
  2. additiondiluted with water
  3. extractionextracted with CH2Cl2
  4. dry with materialThe combined extracts are dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customto give a clear gum residue

Sources & evidence

ORD record
ord-6044220a132240c896fd4424b024fcc3
Source dataset
uspto-grants-2004_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06825212B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes