Ethanolamine → N-(2-hydroxyethyl)-3-[3-(4-fluorophenyl)-1H-pyrazolo[3,4-b]-pyridin-1-yl]phenoxyacetamide

HRID 1084840Notes

Reaction equation

HRID 1084840 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[CH:14][CH:15]=3)[N:10]([C:17]3[CH:18]=[C:19]([CH:25]=[CH:26][CH:27]=3)[O:20][CH2:21][C:22]([OH:24])=O)[N:9]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.C(Cl)(=O)OCC.[CH2:41]([CH2:43][NH2:44])[OH:42]>C(Cl)(Cl)Cl>[OH:42][CH2:41][CH2:43][NH:44][C:22](=[O:24])[CH2:21][O:20][C:19]1[CH:25]=[CH:26][CH:27]=[C:17]([N:10]2[C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:16]3[C:8]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)=[N:9]2)[CH:18]=1

Participants

6

Reactant 4

HCID 700EthanolamineHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 147963983-[3-(4-fluorophenyl)-1H-pyrazolo[3,4-b]pyridin-1-yl]phenoxyacetic acid

Product 1

HCID 15158073N-(2-hydroxyethyl)-3-[3-(4-fluorophenyl)-1H-pyrazolo[3,4-b]-pyridin-1-yl]phenoxyacetamideYield 53.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

In 60 ml of chloroform were dissolved 4.0 g of 3-[3-(4-fluorophenyl)-1H-pyrazolo[3,4-b]pyridin-1-yl]phenoxyacetic acid and 1.3 g of triethylamine. Thereto, 1.4 g of ethyl chlorocarbonate was added at -40° C. The mixture was stirred for 30 minutes. After 0.8 g of ethanolamine was added thereto, the temperature was gradually elevated to room temperature, and the mixture was stirred at room temperature for 2 hours. The reaction mixture was extracted with chloroform. The organic layer was concentrated. The obtained white crude crystals were recrystallized from dioxane to give 2.4 g of N-(2-hydroxyethyl)-3-[3-(4-fluorophenyl)-1H-pyrazolo[3,4-b]-pyridin-1-yl]phenoxyacetamide, m.p. 161°-163° C.

Workup

  1. customwas gradually elevated to room temperature
  2. stirringthe mixture was stirred at room temperature for 2 hours
  3. extractionThe reaction mixture was extracted with chloroform
  4. concentrationThe organic layer was concentrated
  5. customThe obtained white crude crystals were recrystallized from dioxane

Sources & evidence

ORD record
ord-ff3fedd954a147278782f5c260bcddb7
Source dataset
uspto-grants-1991_04
Patent number
US05006520

Reaction notes

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