Hydroxylamine → N-hydroxy-2-(1-pyrrolo[2,3-b]pyridin-1-yl-cyclopentyl)-acetamidine

HRID 2169431Notes

Reaction equation

HRID 2169431 reaction equation
[N:1]1([C:10]2([CH2:15][C:16]#[N:17])[CH2:14][CH2:13][CH2:12][CH2:11]2)[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[CH:2]1.[NH2:18][OH:19].C(OCC)(=O)C>C(O)C.CCCCCC>[OH:19][NH:18][C:16](=[NH:17])[CH2:15][C:10]1([N:1]2[C:5]3=[N:6][CH:7]=[CH:8][CH:9]=[C:4]3[CH:3]=[CH:2]2)[CH2:11][CH2:12][CH2:13][CH2:14]1

Participants

6

Reactant 3

HCID 787HydroxylamineHCID 8857Ethyl AcetateHCID 86726061(1-Pyrrolo[2,3-b]pyridin-1-yl-cyclopentyl)-acetonitrile

Product 1

HCID 178510876N-hydroxy-2-(1-pyrrolo[2,3-b]pyridin-1-yl-cyclopentyl)-acetamidineYield 112.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8058HexaneSolvent

Procedure

To a stirred solution of (1-pyrrolo[2,3-b]pyridin-1-yl-cyclopentyl)-acetonitrile (399) (1.4 g, 6.21 mmol) in ethanol (50 mL) was added 50% aq. NH2OH (4 mL, 62.15 mmol) and the reaction mixture was heated at 60° C. for 16 h (TLC, 30% ethyl acetate in hexane, Rf=0.1). Ethanol was evaporated, water (50 mL) was added and the mixture was extracted with etylacetate (3×50 mL). The organic phase was thereafter dried and concentrated to get crude N-hydroxy-2-(1-pyrrolo[2,3-b]pyridin-1-yl-cyclopentyl)-acetamidine (400) (1.8 g, 112%) as an off-white sticky liquid.

Workup

  1. customEthanol was evaporated
  2. additionwater (50 mL) was added
  3. extractionthe mixture was extracted with etylacetate (3×50 mL)
  4. customThe organic phase was thereafter dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ee46c2dd41af4aacb40d057b0f889d30
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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