Benzylamine → HCID 178433900, compound

HRID 497954Notes

Reaction equation

HRID 497954 reaction equation
[OH:1][C:2]1[C:7]([C:8]([O:10]CC)=O)=[CH:6][N:5]=[C:4]2[N:13]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)[N:14]=[C:15]([CH3:16])[C:3]=12.[CH2:23]([NH2:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C(OCC)(=O)C>[CH2:23]([NH:30][C:8]([C:7]1[C:2]([OH:1])=[C:3]2[C:15]([CH3:16])=[N:14][N:13]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)[C:4]2=[N:5][CH:6]=1)=[O:10])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 178469580HCID 178469580, compound

Product 1

HCID 178433900HCID 178433900, compoundYield 62.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of ethyl 4-hydroxy-3-methyl-1-(2-pyridinyl)-1H-pyrazolo[3,4-b]pyridine-5-carboxylate (2.0 g, 6.7 mmol) and benzylamine (8.0 mL, 73 mmol) was stirred at 180° C. for 16 hours under an argon atmosphere. The mixture was cooled to room temperature, ethyl acetate was added thereto. The resulting crude crystals were collected by filtration, and washed with ethyl acetate. The crude crystals thus obtained were purified by silica gel column chromatography (chloroform:methanol=20:1 to 5:1), and recrystallized from ethanol to give the title compound (1.5 g, 60% yield).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. filtrationThe resulting crude crystals were collected by filtration
  3. washwashed with ethyl acetate
  4. customThe crude crystals thus obtained
  5. customwere purified by silica gel column chromatography (chloroform:methanol=20:1 to 5:1)
  6. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-f174e9efe7d64b6fa2d6e5af5bbfcf66
Source dataset
uspto-grants-2005_09
Patent number
US06949648B2

Reaction notes

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