Thionyl Chloride → 3-(1,4-Diazabicyclo[3.2.1]oct-4-ylcarbonyl)-1H-indazole hydrochloride

HRID 733386Notes

Reaction equation

HRID 733386 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]([OH:12])=O)=[N:2]1.S(Cl)([Cl:15])=O.[N:17]12[CH2:24][CH:21]([CH2:22][CH2:23]1)[NH:20][CH2:19][CH2:18]2>N1C=CC=CC=1>[ClH:15].[N:17]12[CH2:24][CH:21]([CH2:22][CH2:23]1)[N:20]([C:10]([C:3]1[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[NH:1][N:2]=1)=[O:12])[CH2:19][CH2:18]2

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 78250Indazole-3-carboxylic acidHCID 123740771,4-Diazabicyclo[3.2.1]octane

Product 1

HCID 688152363-(1,4-Diazabicyclo[3.2.1]oct-4-ylcarbonyl)-1H-indazole hydrochloride

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A 50 ml reactor is charged with 0.165 g (1.02 mmol) of 1H-indazole-3-carboxylic acid and 1 ml of thionyl chloride and the mixture is heated at ref lux for 1 h 30 min and concentrated under reduced pressure. Then 1.2 ml of pyridine and 0.30 g (2.67 mmol) of 1,4-diazabicyclo[3.2.1]octane are added and the mixture is heated at reflux for 1 h 30 min.

Workup

  1. temperaturethe mixture is heated at ref lux for 1 h 30 min
  2. concentrationconcentrated under reduced pressure
  3. temperaturethe mixture is heated
  4. temperatureat reflux for 1 h 30 min.

Sources & evidence

ORD record
ord-d760af6bae744b98a854959c36e95f07
Source dataset
uspto-grants-2009_09
Patent number
US07589201B2

Reaction notes

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