Trifluoroacetic acid → HCID 59333536, compound

HRID 1876621Notes

Reaction equation

HRID 1876621 reaction equation
[CH3:1][C@H:2]1[CH2:7][O:6][CH2:5][CH2:4][N:3]1[C:8]1[N:16]=[C:15]([C:17]2[CH:18]=[N:19][C:20]([NH:23]C(=O)OC(C)(C)C)=[N:21][CH:22]=2)[N:14]=[C:13]2[C:9]=1[N:10]=[C:11]([N:36]1[CH2:41][CH2:40][N:39]([S:42]([CH3:45])(=[O:44])=[O:43])[CH2:38][CH2:37]1)[N:12]2[CH2:31][C:32]([F:35])([F:34])[F:33].FC(F)(F)C(O)=O>C(Cl)Cl>[CH3:1][C@H:2]1[CH2:7][O:6][CH2:5][CH2:4][N:3]1[C:8]1[N:16]=[C:15]([C:17]2[CH:18]=[N:19][C:20]([NH2:23])=[N:21][CH:22]=2)[N:14]=[C:13]2[C:9]=1[N:10]=[C:11]([N:36]1[CH2:37][CH2:38][N:39]([S:42]([CH3:45])(=[O:44])=[O:43])[CH2:40][CH2:41]1)[N:12]2[CH2:31][C:32]([F:34])([F:33])[F:35]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59333602HCID 59333602, compound

Product 1

HCID 59333536HCID 59333536, compoundYield 83.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A methylene chloride (5 ml) solution of tert-butyl (5-{6-[(3S)-3-methylmorpholin-4-yl]-8-[4-(methylsulfonyl)piperazin-1-yl]-9-(2,2,2-trifluoroethyl)-9H-purin-2-yl}pyrimidin-2-yl)carbamate (199 mg, 0.30 mmol) and trifluoroacetic acid (1 ml) was stirred at room temperature for 1.5 hours and concentrated under reduced pressure. Chloroform and saturated aqueous sodium hydrogen carbonate solution were added to the residue and the resulting mixture was extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate and, after filtration, the filtrate was concentrated under reduced pressure. The residue was purified by flash silica gel column chromatography (methylene chloride:methanol=96:4) to give a solid. The resulting solid was washed with ether-hexane and dried to give the title compound (140 mg, 83%) as a powder.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionChloroform and saturated aqueous sodium hydrogen carbonate solution were added to the residue
  3. extractionthe resulting mixture was extracted with chloroform
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. filtrationafter filtration
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe residue was purified by flash silica gel column chromatography (methylene chloride:methanol=96:4)
  8. customto give a solid
  9. washThe resulting solid was washed with ether-hexane
  10. customdried

Sources & evidence

ORD record
ord-88b5a452436249f7aac147f959aae956
Source dataset
uspto-grants-2012_11
Patent number
US08309546B2

Reaction notes

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