HCID 68663654, compound → HCID 68663709, compound

HRID 452769Notes

Reaction equation

HRID 452769 reaction equation
[C:1]1([CH2:7][CH2:8][C:9]2[NH:21][C:12]3[N:13]=[CH:14][CH:15]=[C:16]([C:17]([NH:19][NH2:20])=[O:18])[C:11]=3[CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:22]([O-])([O-])(OCC)[CH3:23]>>[CH3:22][C:23]1[O:18][C:17]([C:16]2[CH:15]=[CH:14][N:13]=[C:12]3[NH:21][C:9]([CH2:8][CH2:7][C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)=[CH:10][C:11]=23)=[N:19][N:20]=1

Participants

3

Reactant 2

HCID 68663654HCID 68663654, compoundHCID 86598186Ethyl ortho-acetate

Product 1

HCID 68663709HCID 68663709, compoundYield 75%

Conditions

Temperature
140 °C

Procedure

A mixture of 2-(2-phenylethyl)-1H-pyrrolo[2,3-b]pyridine-4-carbohydrazide (104 mg, 0.371 mmol) and ethyl orthoacetate (5 mL) was stirred at 120° C. for 1 hr and at 140° C. for 1 hr. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1-0/1) and basic silica gel column chromatography (hexane/ethyl acetate=4/1-0/1), and recrystallized from hexane/ethyl acetate to give the title compound (85 mg, yield 75%) as pale-yellow crystals.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1-0/1) and basic silica gel column chromatography (hexane/ethyl acetate=4/1-0/1)
  3. customrecrystallized from hexane/ethyl acetate

Sources & evidence

ORD record
ord-4edd1f2f176c4d51988b665552ca01d7
Source dataset
uspto-grants-2013_07
Patent number
US08492378B2

Reaction notes

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