Indazole-3-carboxylic acid → HCID 14999062, compound

HRID 374108Notes

Reaction equation

HRID 374108 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]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:18][CH:17]([CH3:28])[N:16]([CH3:29])[CH2:15]1>CN(C)C=O>[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]([CH3:29])[CH:17]([CH3:28])[CH2:18]1)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

4

Reactant 2

HCID 78250Indazole-3-carboxylic acidHCID 14999061HCID 14999061, compound

Product 1

HCID 14999062HCID 14999062, compoundYield 18.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
60 °C

Procedure

To a solution of 1H-indazole-3-carboxylic acid (2.2 g) in N,N-dimethylformamide (40 ml), N,N'-carbonyldiimidazole (2.2 g) is added, and the mixture is heated at 60° C. for 3.5 hours. A solution of 6-amino-1-benzyl-3,4-dimethylhexahydro-1H-1,4-diazepine (3.0 g) in N,N-dimethylformamide (10 ml) is added to the mixture, and the mixture is stirred at 25° 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 10% aqueous sodium hydroxide solution, water and saturated aqueous sodium chloride solution, and dried over sodium sulfate. The solvent is evaporated under reduced pressure, and the residue is chromatographed on silica gel with elution 10% methanol-acetone. Fractions containing the title compound are pooled and evaporated under reduced pressure to give the title compound (0.9 g) which is one isomer with lower polarity in two isomers produced in the above reaction, m.p. 203°-205° C. (recrystallized from isopropyl alcohol).

Workup

  1. customThe solvent is evaporated under reduced pressure
  2. additionthe residue is diluted with water
  3. extractionextracted with chloroform
  4. washThe organic layer is washed successively with 10% aqueous sodium hydroxide solution, water and saturated aqueous sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. customThe solvent is evaporated under reduced pressure
  7. customthe residue is chromatographed on silica gel with elution 10% methanol-acetone
  8. additionFractions containing the title compound
  9. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-d75a18d3bdd94d3282ac3c73567cf019
Source dataset
uspto-grants-1992_11
Patent number
US05166341

Reaction notes

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