Indazole-3-carboxylic acid → HCID 14999040, compound

HRID 374102Notes

Reaction equation

HRID 374102 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.[NH2:13][CH:14]1[CH2:20][N:19]([CH2:21][C:22]2[CH:27]=[C:26]([CH3:28])[CH:25]=[CH:24][C:23]=2[CH3:29])[CH2:18][CH2:17][N:16]([CH3:30])[CH2:15]1>CN(C)C=O>[CH3:29][C:23]1[CH:24]=[CH:25][C:26]([CH3:28])=[CH:27][C:22]=1[CH2:21][N:19]1[CH2:20][CH:14]([NH:13][C:10]([C:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[NH:1][N:2]=2)=[O:12])[CH2:15][N:16]([CH3:30])[CH2:17][CH2:18]1

Participants

4

Reactant 2

HCID 78250Indazole-3-carboxylic acidHCID 14999038HCID 14999038, compound

Product 1

HCID 14999040HCID 14999040, compoundYield 67.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 1H-indazole-3-carboxylic acid (1.0 g) in N,N-dimethylformamide (20 ml), N,N'-carbonyldiimidazole (1.1 g) is added, and the mixture is heated at 60° C. for 2 hours. 6-Amino-1-(2,5-dimethylbenzyl)-4-methylhexahydro-1H-1,4-diazepine (1.5 g) is added to the reaction mixture, and the mixture is heated at 60° C. for 2 hours. The solvent is evaporated under reduced pressure, and the residue is diluted with water and extracted with chloroform. The organic layer is washed successively with water and aqueous sodium hydroxide solution, and dried over sodium sulfate. The solvent is evaporated under reduced pressure, and the residue is chromatographed on silica gel with elution of acetone. Fractions containing the title compound are pooled and evaporated under reduced pressure to give the title compound (1.6 g) as an oil. The free base thus obtained is converted to the fumarate of the title compound in a usual manner, m.p. 168°-170° C. (recrystallized from ethanol).

Workup

  1. temperaturethe mixture is heated at 60° C. for 2 hours
  2. customThe solvent is evaporated under reduced pressure
  3. additionthe residue is diluted with water
  4. extractionextracted with chloroform
  5. washThe organic layer is washed successively with water and aqueous sodium hydroxide solution
  6. dry with materialdried over sodium sulfate
  7. customThe solvent is evaporated under reduced pressure
  8. customthe residue is chromatographed on silica gel with elution of acetone
  9. additionFractions containing the title compound
  10. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-d9ae757b9b584b3d9a395e4113ddcc04
Source dataset
uspto-grants-1992_11
Patent number
US05166341

Reaction notes

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