Acetic Anhydride → HCID 178476705, compound

HRID 2169432Notes

Reaction equation

HRID 2169432 reaction equation
C([O:4][C:5](=[O:7])[CH3:6])(=O)C.O[NH:9][C:10](=[NH:26])[CH2:11][C:12]1([N:17]2[C:21]3=[N:22][CH:23]=[CH:24][CH:25]=[C:20]3[CH:19]=[CH:18]2)[CH2:16][CH2:15][CH2:14][CH2:13]1.C(OCC)(=O)C.C([O-])(O)=O.[Na+]>O>[C:5]([O:4][NH:26][C:10](=[NH:9])[CH2:11][C:12]1([N:17]2[C:21]3=[N:22][CH:23]=[CH:24][CH:25]=[C:20]3[CH:19]=[CH:18]2)[CH2:13][CH2:14][CH2:15][CH2:16]1)(=[O:7])[CH3:6]

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 178510876N-hydroxy-2-(1-pyrrolo[2,3-b]pyridin-1-yl-cyclopentyl)-acetamidine

Product 1

HCID 178476705HCID 178476705, compoundYield 81.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Acetic anhydride (11.2 mL, 118.61 mmol) was added to N-hydroxy-2-(1-pyrrolo[2,3-b]pyridin-1-yl-cyclopentyl)-acetamidine (400) (1.8 g, 6.98 mmol) and stirring was continued for 3 h at room temperature (TLC, ethyl acetate, Rf=0.5). Water (50 mL) was added, and the mixture was basified to pH 8 by solid NaHCO3 and extracted with ethyl acetate (3×50 mL). The organic phase was thereafter dried and concentrated. The crude product was purified by Combi-Flash column (eluted at 20-30% ethyl acetate in hexane) to get 2-(1-{1H-pyrrolo[2,3-b]pyridin-1-yl}cyclopentyl)ethanimidamido acetate (401) (1.7 g, 81%) as an off-white solid.

Workup

  1. extractionextracted with ethyl acetate (3×50 mL)
  2. customThe organic phase was thereafter dried
  3. concentrationconcentrated
  4. customThe crude product was purified by Combi-Flash column (eluted at 20-30% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-c03b5e09363340d18e9e2d6c19c0d00d
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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