Potassium Carbonate → HCID 18447422, compound

HRID 1269899Notes

Reaction equation

HRID 1269899 reaction equation
C(=O)([O-])[O-].[K+].[K+].[O:7]([CH2:14][CH2:15]Br)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH:17]12[NH:24][CH:21]([CH2:22][CH2:23]1)[CH2:20][CH:19]([NH:25][C:26]1[CH:27]=[C:28]3[C:32](=[CH:33][CH:34]=1)[NH:31][N:30]=[CH:29]3)[CH2:18]2>CN(C)C=O>[O:7]([CH2:14][CH2:15][N:24]1[CH:21]2[CH2:22][CH2:23][CH:17]1[CH2:18][CH:19]([NH:25][C:26]1[CH:27]=[C:28]3[C:32](=[CH:33][CH:34]=1)[NH:31][N:30]=[CH:29]3)[CH2:20]2)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 68526Benzene, (2-bromoethoxy)-HCID 18447426HCID 18447426, compound

Product 1

HCID 18447422HCID 18447422, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (52 mg, 0.376 mmol) and then 2-phenoxyethyl bromide (38 mg, 0.189 mmol) were added to a suspension of the N-(8-azabicyclo[3.2.1]oct-3-yl)-1H-indazol-5-amine (30 mg, 0.124 mmol) obtained in Example 525 in dimethylformamide (1 ml), and the resulting mixture was stirred at room temperature for 20 hours. After the solid was removed by filtration, the dimethylformamide was distilled off under reduced pressure as an azeotrope with toluene to obtain a crude product. The crude product was purified by a silica gel column chromatography (eluent: chloroform/methanol/triethylamine=20/1/1) to obtain N-(8-(2-phenoxyethyl)-8-azabicyclo[3.2.1]oct-3-yl)-1H-indazol-5-amine (40 mg, 89%).

Workup

  1. customAfter the solid was removed by filtration
  2. distillationthe dimethylformamide was distilled off under reduced pressure as an azeotrope with toluene
  3. customto obtain a crude product
  4. customThe crude product was purified by a silica gel column chromatography (eluent: chloroform/methanol/triethylamine=20/1/1)

Sources & evidence

ORD record
ord-faa2a53309744de79a782d7574ec100b
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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