Trifluoroacetic acid → HCID 67449594, compound

HRID 2370073Notes

Reaction equation

HRID 2370073 reaction equation
FC(F)(F)C(O)=O.[Cl:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[N:16]([CH2:32][CH2:33][NH:34]C(=O)OC(C)(C)C)[C:17]2[C:22]([N:23]=1)=[C:21]([N:24]1[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][CH2:25]1)[N:20]=[C:19]([CH3:31])[N:18]=2>ClCCl>[Cl:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[N:16]([CH2:32][CH2:33][NH2:34])[C:17]2[C:22]([N:23]=1)=[C:21]([N:24]1[CH2:25][CH2:26][N:27]([CH3:30])[CH2:28][CH2:29]1)[N:20]=[C:19]([CH3:31])[N:18]=2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67448282HCID 67448282, compound

Product 1

HCID 67449594HCID 67449594, compoundYield 101.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add trifluoroacetic acid (5 mL) to a solution of tert-butyl N-[2-[8-(2-chlorophenyl)-2-methyl-6-(4-methylpiperazin-1-yl)purin-9-yl]ethyl]carbamate (0.51 g, 0.001 mol) in dichloromethane (5 mL) at 0° C. Allow the reaction to warm to room temperature and stir for 2 h. Quench the reaction mixture with saturated aqueous sodium bicarbonate solution and then extract with dichloromethane. Dry the organic layer over anhydrous sodium sulfate, filter, and concentrate to give 2-[8-(2-chlorophenyl)-2-methyl-6-(4-methylpiperazin-1-yl)purin-9-yl]ethanamine (0.39 g). ES/MS m/z 386 (M+1).

Workup

  1. customthe reaction
  2. customQuench the reaction mixture with saturated aqueous sodium bicarbonate solution
  3. extractionextract with dichloromethane
  4. dry with materialDry the organic layer over anhydrous sodium sulfate
  5. filtrationfilter
  6. concentrationconcentrate

Sources & evidence

ORD record
ord-9901a2f4997549359ce104f168d72164
Source dataset
uspto-grants-2014_04
Patent number
US08710063B2

Reaction notes

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