Cyclopropylamine → HCID 9884809, compound

HRID 1392114Notes

Reaction equation

HRID 1392114 reaction equation
Cl[C:2]1[N:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[F:22].[NH2:23][CH:24]1[CH2:26][CH2:25]1>CCO>[CH:24]1([NH:23][C:2]2[N:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[N:8]=[C:7]3[C:3]=2[N:4]=[CH:5][N:6]3[CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[F:22])[CH2:26][CH2:25]1

Participants

4

Reactant 2

HCID 69828CyclopropylamineHCID 100880509H-Purine, 6-chloro-9-[(2-fluorophenyl)methyl]-2-(trifluoromethyl)-

Product 1

HCID 9884809HCID 9884809, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 100 mg (0.30 mmol) of 6-chloro-9-(2-fluorobenzyl)-2-trifluoromethylpurine, 1 mL (14 mmol) of aminocyclopropane, and 5 mL of EtOH were stirred at room temperature for 16 hours. The reaction mixture was concentrated in vacuo and the residue was dissolved in CH2Cl2, washed with 2×5 mL H2O, 5 mL brine, dried (Na2SO4), and concentrated. Chromatography over silica gel using 33% EtOAc in hexanes as eluant provided 102 mg (97% yield) of the desired product. M.P. 118.5-119.0° C.; 1H NMR (CDCl3) δ 7.892 (s, 1H), 7.50-7.39 (m, 1H), 7.37-7.29 (m, 1H), 7.18-7.05 (m, 2H), 5.95 (bs, 1H), 5.44 (s, 2H), 0.94-0.91 (m, 2H), 0.65-0.64 (m, 2H).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionthe residue was dissolved in CH2Cl2
  3. washwashed with 2×5 mL H2O, 5 mL brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-f46ad453a51948f986c0628ec489c484
Source dataset
uspto-grants-2008_03
Patent number
US07342021B2

Reaction notes

Loading…