Triethylamine → HCID 86704981, compound

HRID 572170Notes

Reaction equation

HRID 572170 reaction equation
Cl[C:2]1[NH:6][C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[N:3]=1.[OH:11][C:12]1[CH:17]=[CH:16][C:15]([N:18]2[C:22]3=[N:23][CH:24]=[CH:25][CH:26]=[C:21]3[C:20](=[O:27])[N:19]2[CH3:28])=[CH:14][CH:13]=1.C(N(CC)CC)C>CO>[NH:3]1[C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=[C:2]1[O:11][C:12]1[CH:13]=[CH:14][C:15]([N:18]2[C:22]3=[N:23][CH:24]=[CH:25][CH:26]=[C:21]3[C:20](=[O:27])[N:19]2[CH3:28])=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 785722-ChlorobenzimidazoleHCID 86704980HCID 86704980, compound

Product 1

HCID 86704981HCID 86704981, compoundYield 13.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 2-chloro-1H-benzimidazole (0.057 g), 1-(4-hydroxyphenyl)-2-methyl-1,2-dihydro-3H-pyrazolo[3,4-b]pyridin-3-one (0.060 g) and triethylamine (3.5 ml) was stirred under a nitrogen atmosphere at 160° C. for 16 hr. The reaction mixture was cooled to room temperature, diluted with methanol, and silica gel was added. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (0.012 g).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. additionwas added
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-76bdd5cbab7d403e9c09fec8a8521527
Source dataset
uspto-grants-2015_05
Patent number
US09029388B2

Reaction notes

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