Trifluoroacetic acid → HCID 67446836, compound

HRID 2370071Notes

Reaction equation

HRID 2370071 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]([CH2:33][CH2:34][NH:35]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]([CH2:30][CH3:31])[CH2:26][CH2:25]1)[N:20]=[C:19]([CH3:32])[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]([CH2:33][CH2:34][NH2:35])[C:17]2[C:22]([N:23]=1)=[C:21]([N:24]1[CH2:25][CH2:26][N:27]([CH2:30][CH3:31])[CH2:28][CH2:29]1)[N:20]=[C:19]([CH3:32])[N:18]=2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67448920HCID 67448920, compound

Product 1

HCID 67446836HCID 67446836, compoundYield 62.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add trifluoroacetic acid (3 mL) to a solution of tert-butyl N-[2-[8-(2-chlorophenyl)-6-(4-ethylpiperazin-1-yl)-2-methyl-purin-9-yl]ethyl]carbamate (0.6 g, 1.2 mmol) in dichloromethane (3 mL) at 0° C. and stir for 2 h at room temperature. Quench the reaction mixture with saturated aqueous sodium bicarbonate solution, and extract with dichloromethane. Dry the organic layer over anhydrous sodium sulfate, filter, and concentrate to give a residue. Purify the residue on a silica gel column using dichloromethane-methanol (96:4) as eluent to give 2-[8-(2-chlorophenyl)-6-(4-ethylpiperazin-1-yl)-2-methyl-purin-9-yl]ethanamine (0.3 g). ES/MS m/z 400 (M+1).

Workup

  1. customQuench the reaction mixture with saturated aqueous sodium bicarbonate solution
  2. extractionextract with dichloromethane
  3. dry with materialDry the organic layer over anhydrous sodium sulfate
  4. filtrationfilter
  5. concentrationconcentrate
  6. customto give a residue
  7. customPurify the residue on a silica gel column

Sources & evidence

ORD record
ord-0679ca1dd4574155b1a8458705f2b1ec
Source dataset
uspto-grants-2014_04
Patent number
US08710063B2

Reaction notes

Loading…