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Methylamine → N-methyl-1-(4-{5-[3-(trifluoromethyl)-4-(2,2,2-trifluoro-1-methylethoxy)phenyl]-1,2,4-oxadiazol-3-yl}-1H-indol-3-yl)methanamine

HRID 2244645
Notes
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Reaction equation

HRID 2244645 reaction equation
[F:1][C:2]([F:33])([F:32])[C:3]1[CH:4]=[C:5]([C:16]2[O:20][N:19]=[C:18]([C:21]3[CH:29]=[CH:28][CH:27]=[C:26]4[C:22]=3[C:23]([CH:30]=O)=[CH:24][NH:25]4)[N:17]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH:10]([CH3:15])[C:11]([F:14])([F:13])[F:12].[CH3:34][NH2:35]>CO>[CH3:34][NH:35][CH2:30][C:23]1[C:22]2[C:26](=[CH:27][CH:28]=[CH:29][C:21]=2[C:18]2[N:17]=[C:16]([C:5]3[CH:6]=[CH:7][C:8]([O:9][CH:10]([CH3:15])[C:11]([F:14])([F:12])[F:13])=[C:3]([C:2]([F:33])([F:32])[F:1])[CH:4]=3)[O:20][N:19]=2)[NH:25][CH:24]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 6329MethylamineHCID 592144034-{5-[3-(trifluoromethyl)-4-(2,2,2-trifluoro-1-methylethoxy)phenyl]-1,2,4-oxadiazol-3-yl}-1H-indole-3-carboaldehyde

Product 1

HCID 59214308N-methyl-1-(4-{5-[3-(trifluoromethyl)-4-(2,2,2-trifluoro-1-methylethoxy)phenyl]-1,2,4-oxadiazol-3-yl}-1H-indol-3-yl)methanamineYield 56.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of 4-{5-[3-(trifluoromethyl)-4-(2,2,2-trifluoro-1-methylethoxy)phenyl]-1,2,4-oxadiazol-3-yl}-1H-indole-3-carboaldehyde (150.0 mg) in CH3OH (1.5 ml) was added a 40% CH3OH solution of CH3NH2 (74.5 mg) at 0° C. After warming to room temperature, the solution was stirred at room temperature for 3 hours. After confirming the production of an iminium salt, the organic solvent was evaporated under reduced pressure. The residue was dissolved in EtOH (1.5 ml). To this was added NaBH4 (12.09 mg) at 0° C. After warming to room temperature, the solution was stirred at room temperature for 15 hours. To the reaction solution was added water (30 ml), followed by extraction three times with EtOAc (20 ml). The organic layer was combined, washed with saturated brine, dried over anhydrous MgSO4, and then filtered, and the filtrate was concentrated. The residue was purified by silica gel column chromatography (automatic purifier, chloroform:CH3OH=100:0 to 90:10) to obtain N-methyl-1-(4-{5-[3-(trifluoromethyl)-4-(2,2,2-trifluoro-1-methylethoxy)phenyl]-1,2,4-oxadiazol-3-yl}-1H-indol-3-yl)methanamine (87.4 mg) as a white solid.

Workup

  1. customthe organic solvent was evaporated under reduced pressure
  2. dissolutionThe residue was dissolved in EtOH (1.5 ml)
  3. additionTo this was added NaBH4 (12.09 mg) at 0° C
  4. temperatureAfter warming to room temperature
  5. stirringthe solution was stirred at room temperature for 15 hours
  6. additionTo the reaction solution was added water (30 ml)
  7. extractionfollowed by extraction three times with EtOAc (20 ml)
  8. washwashed with saturated brine
  9. dry with materialdried over anhydrous MgSO4
  10. filtrationfiltered
  11. concentrationthe filtrate was concentrated
  12. customThe residue was purified by silica gel column chromatography (automatic purifier, chloroform:CH3OH=100:0 to 90:10)

Sources & evidence

ORD record
ord-5411d6b5036a46448fb0f1c46e9f54ff
Source dataset
uspto-grants-2010_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07678820B2

Reaction notes

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