Trifluoroacetic acid → HCID 178420327, compound

HRID 1809713Notes

Reaction equation

HRID 1809713 reaction equation
[CH2:1]([NH:8][C:9]1[N:14]=[C:13]([C:15]2[C:23]3[C:18](=[N:19][C:20]([NH:24][CH2:25][CH2:26][N:27]4[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]4)=[N:21][CH:22]=3)[N:17](COCC[Si](C)(C)C)[N:16]=2)[CH:12]=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(C(O)=O)(F)(F)F>ClCCl>[CH2:1]([NH:8][C:9]1[N:14]=[C:13]([C:15]2[C:23]3[C:18](=[N:19][C:20]([NH:24][CH2:25][CH2:26][N:27]4[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]4)=[N:21][CH:22]=3)[NH:17][N:16]=2)[CH:12]=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68109557[3-(6-benzylamino-pyridin-2-yl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-d]pyrimidin-6-yl]-(2-piperidin-1-yl-ethyl)-amine

Product 1

HCID 178420327HCID 178420327, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of [3-(6-benzylamino-pyridin-2-yl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-d]pyrimidin-6-yl]-(2-piperidin-1-yl-ethyl)-amine (133 mg, 0.24 mmol) in dichloromethane (2 mL) was added CF3CO2H (3 mL). This mixture was stirred at room temperature for 3 hours. The reaction was quenched by adding saturated aqueous NaHCO3 to pH about 9, and then extracted with dichloromethane (3×20 mL). The combined organic phase was dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. The residue was washed with EtOAc (4 mL) and dried to give [3-(6-benzylamino-pyridin-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-6-yl]-(2-piperidin-1-yl-ethyl)-amine as a white solid. (Yield 78 mg, 76%).

Workup

  1. customThe reaction was quenched
  2. additionby adding saturated aqueous NaHCO3 to pH about 9
  3. extractionextracted with dichloromethane (3×20 mL)
  4. dry with materialThe combined organic phase was dried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. washThe residue was washed with EtOAc (4 mL)
  8. customdried

Sources & evidence

ORD record
ord-e8791bbed0fe43ff8d2c919148e230cc
Source dataset
uspto-grants-2013_01
Patent number
US08362023B2

Reaction notes

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