1,1'-Carbonyldiimidazole → HCID 10494466, compound

HRID 2256358Notes

Reaction equation

HRID 2256358 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.C(N1C=CN=C1)(N1C=CN=C1)=O.[NH2:25][CH2:26][CH2:27][CH2:28][CH2:29][N:30]1[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1>CN(C)C=O>[N:30]1([CH2:29][CH2:28][CH2:27][CH2:26][NH:25][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])[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 78250Indazole-3-carboxylic acidHCID 64841444-Piperidin-1-yl-butylamine

Product 1

HCID 10494466HCID 10494466, compoundYield 101.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 1H-indazole-3-carboxylic acid (0.745 g, 4.6 mmol) in 20 mL dimethylformamide, was added 1,1'-carbonyldiimidazole (0.745 g, 4.6 mmol). This mixture was stirred at room temperature for 4 h, and to it was added dropwise a solution of 1-(4-aminobutyl)piperidine (0.718 g, 4.6 mmol) dissolved in 3 mL dimethylformamide. This solution was then stirred at room temperature for 18 h, the volatiles were evaporated and the residue was diluted with water. Extraction with ethyl acetate followed by water and brine washes gave 1.40 g of an oil which was sufficiently pure for use in the next reaction. Mass spectrum, m+ =301.

Workup

  1. stirringThis solution was then stirred at room temperature for 18 h
  2. customthe volatiles were evaporated
  3. additionthe residue was diluted with water
  4. extractionExtraction with ethyl acetate

Sources & evidence

ORD record
ord-4c20c45620ad4d60a1550c465afbd822
Source dataset
uspto-grants-1997_08
Patent number
US05654320

Reaction notes

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