Trifluoroacetic acid → HCID 118023453, compound

HRID 2171789Notes

Reaction equation

HRID 2171789 reaction equation
[CH3:1][C:2]1([CH3:33])[CH2:7][CH2:6][CH:5]([C:8]2[S:9][C:10]3[N:11]=[C:12]([CH3:32])[N:13]=[C:14]([CH2:17][N:18]4[CH2:23][C@@H:22]5[CH2:24][C@H:19]4[CH2:20][N:21]5C(OC(C)(C)C)=O)[C:15]=3[N:16]=2)[CH2:4][CH2:3]1.FC(F)(F)C(O)=O.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[C@H:19]12[CH2:24][C@H:22]([NH:21][CH2:20]1)[CH2:23][N:18]2[CH2:17][C:14]1[C:15]2[N:16]=[C:8]([CH:5]3[CH2:6][CH2:7][C:2]([CH3:33])([CH3:1])[CH2:3][CH2:4]3)[S:9][C:10]=2[N:11]=[C:12]([CH3:32])[N:13]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 118029554HCID 118029554, compound

Product 1

HCID 118023453HCID 118023453, compoundYield 88.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To tert-butyl (1S,4S)-5-{[2-(4,4-dimethylcyclohexyl)-5-methyl[1,3]thiazolo[5,4-d]pyrimidin-7-yl]methyl}-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate (476 mg) and DCM (10 mL) was added trifluoroacetic acid (2.0 mL), followed by stirring at room temperature for 2 hours. To the reaction mixture was added saturated aqueous sodium bicarbonate, followed by extraction with EtOAc. The organic layer was washed with brine, dried over Na2SO4, and then concentrated under reduced pressure. The residue was purified by silica gel column to obtain 7-[(1S,4S)-2,5-diazabicyclo[2.2.1]hept-2-ylmethyl]-2-(4,4-dimethylcyclohexyl)-5-methyl[1,3]thiazolo[5,4-d]pyrimidine (332 mg).

Workup

  1. extractionfollowed by extraction with EtOAc
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column

Sources & evidence

ORD record
ord-a5ff24c01e034c94a57f7daf0ae2df07
Source dataset
uspto-grants-2015_06
Patent number
US09051339B2

Reaction notes

Loading…