Acetic Acid → HCID 178419479, compound

HRID 1349887Notes

Reaction equation

HRID 1349887 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.COC(OC)[N:23]([CH3:25])C.C(O)(=O)C.[NH2:32]N>O>[NH:23]1[CH:25]=[N:32][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:13]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 9321HydrazineHCID 78373Dimethylformamide dimethyl acetalHCID 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 dimethyl 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-0a9e2c9ee0f54b9ea2ebd00a4e40fb77
Source dataset
uspto-grants-2007_05
Patent number
US07211594B2

Reaction notes

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