HCID 178476705, compound → Acetic acid;2-(1-pyrrolo[2,3-b]pyridin-1-ylcyclopentyl)ethanimidamide

HRID 2169433Notes

Reaction equation

HRID 2169433 reaction equation
[C:1]([O:4][NH:5][C:6](=[NH:22])[CH2:7][C:8]1([N:13]2[C:17]3=[N:18][CH:19]=[CH:20][CH:21]=[C:16]3[CH:15]=[CH:14]2)[CH2:12][CH2:11][CH2:10][CH2:9]1)(=[O:3])[CH3:2]>C(O)C.[Pd]>[C:1]([OH:4])(=[O:3])[CH3:2].[N:13]1([C:8]2([CH2:7][C:6]([NH2:22])=[NH:5])[CH2:12][CH2:11][CH2:10][CH2:9]2)[C:17]2=[N:18][CH:19]=[CH:20][CH:21]=[C:16]2[CH:15]=[CH:14]1

Participants

4

Reactant 1

HCID 178476705HCID 178476705, compound

Product 1

HCID 86726064Acetic acid;2-(1-pyrrolo[2,3-b]pyridin-1-ylcyclopentyl)ethanimidamideYield 87%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a stirred degassed solution of 2-(1-{1H-pyrrolo[2,3-b]pyridin-1-yl}cyclopentyl)ethanimidamido acetate (401) (500 mg, 1.67 mmol) in ethanol (20 mL) was added 10% Pd—C (50 mg) and stirring was continued 30 min under H2 (hydrogen-bludder) at room temperature (TLC, 50% ethyl acetate in hexane, Rf=0.1), The reaction mixture was filtered through a celite bed and washed with 10% methanol in dichloromethane (5×50 mL). The organic phase was thereafter dried and concentrated to get 2-(1-pyrrolo[2,3-b]pyridin-1-yl-cyclopentyl)-acetamidine; compound with acetic acid (402) (437 mg, 87%) as an off-white solid.

Workup

  1. filtration(TLC, 50% ethyl acetate in hexane, Rf=0.1), The reaction mixture was filtered through a celite bed
  2. washwashed with 10% methanol in dichloromethane (5×50 mL)
  3. customThe organic phase was thereafter dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a782512180134d60882af8a4e35b4856
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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