Acetic Acid → HCID 178419479, compound

HRID 1353941Notes

Reaction equation

HRID 1353941 reaction equation
[Br:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]([NH2:13])=O)[CH:9]=2)[N:4]([CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][O:15]2)[N:3]=1.[C:20](O)(=O)C.[NH2:24][NH2:25]>O>[NH:24]1[CH:20]=[N:13][C:11]([C:8]2[CH:9]=[C:10]3[C:5](=[CH:6][CH:7]=2)[N:4]([CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][O:15]2)[N:3]=[C:2]3[Br:1])=[N:25]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 9321HydrazineHCID 224799153-bromo-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-5-carboxamide

Product 1

HCID 178419479HCID 178419479, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

The title compound was prepared by reacting 3-bromo-1-perhydro-2H-pyran-2-yl-1H-indazole-5-carboxamide (15.13 g, 46.67 mmol) with N,N-dimethylformamide dimethlyl acetal (134 mL) and heating to 80° C. for 3 hours. The reaction was allowed to cool to room temperature, and condensed to a brown oil that was exposed to atmospheric conditions minimally. To the crude oil was added glacial acetic acid (220 mL) and hydrazine (23 mL), and then the mixture was heated to 115° C. for 1.5 hours. The reaction was allowed to cool to room temperature, and subsequently added to water (500 mL) resulting in the formation of a white precipitate which was filtered and dried in a vacuum oven (15.05 g, 93% yield): ES-MS (m/z) 350 [M+1]+.

Workup

  1. temperatureto cool to room temperature
  2. customcondensed to a brown oil that
  3. temperaturethe mixture was heated to 115° C. for 1.5 hours
  4. temperatureto cool to room temperature
  5. customresulting in the formation of a white precipitate which
  6. filtrationwas filtered
  7. customdried in a vacuum oven (15.05 g, 93% yield)

Sources & evidence

ORD record
ord-8484497f02954a70b4f4e6f5ebf5992c
Source dataset
uspto-grants-2007_05
Patent number
US07220771B2

Reaction notes

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