Trifluoroacetic acid → HCID 178420328, compound

HRID 1809716Notes

Reaction equation

HRID 1809716 reaction equation
[CH2:1]([NH:8][C:9]1[CH:10]=[C:11]([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][O:30][CH2:29][CH2:28]4)=[N:21][CH:22]=3)[N:17](COCC[Si](C)(C)C)[N:16]=2)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1(CCNC2N=C3N(COCC[Si](C)(C)C)N=C(C4C=CC=CC=4)C3=CN=2)CCOCC1.C(O)(C(F)(F)F)=O>ClCCl>[CH2:1]([NH:8][C:9]1[CH:10]=[C:11]([C:15]2[C:23]3[C:18](=[N:19][C:20]([NH:24][CH2:25][CH2:26][N:27]4[CH2:28][CH2:29][O:30][CH2:31][CH2:32]4)=[N:21][CH:22]=3)[NH:17][N:16]=2)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 68108377HCID 68108377, compoundHCID 68109149HCID 68109149, compound

Product 1

HCID 178420328HCID 178420328, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of a mixture of [3-(3-benzylamino-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-d]pyrimidin-6-yl]-(2-morpholin-4-yl-ethyl)-amine and (2-morpholin-4-yl-ethyl)-[3-phenyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-d]pyrimidin-6-yl]-amine (210 mg, crude) in dichloromethane (5 mL) was added TFA (5 mL) at room temperature. The resulting mixture was stirred for another three hours at this temperature. The solvent was evaporated under reduced pressure and the residue was treated with saturated aqueous NaHCO3 (3 mL) and extracted with EtOAc (10 mL). The organic phase was washed with brine (5 mL) and dried to give crude product. It was purified by prep-HPLC to give [3-(3-benzylamino-phenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-yl]-(2-morpholin-4-yl-ethyl)-amine as yellow solid. (Yield 24 mg, 14.9%).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. additionthe residue was treated with saturated aqueous NaHCO3 (3 mL)
  3. extractionextracted with EtOAc (10 mL)
  4. washThe organic phase was washed with brine (5 mL)
  5. customdried
  6. customto give crude product
  7. customIt was purified by prep-HPLC

Sources & evidence

ORD record
ord-df92ea6bb288467cab730e14bfb20c48
Source dataset
uspto-grants-2013_01
Patent number
US08362023B2

Reaction notes

Loading…