Trifluoroacetic acid → HCID 178420614, compound

HRID 1809727Notes

Reaction equation

HRID 1809727 reaction equation
[N:1]1([CH2:7][CH2:8][NH:9][C:10]2[N:15]=[C:14]3[N:16](COCC[Si](C)(C)C)[N:17]=[C:18]([C:19]4[CH:24]=[CH:23][CH:22]=[C:21]([NH:25][CH2:26][C:27]5[S:28][CH:29]=[CH:30][CH:31]=5)[CH:20]=4)[C:13]3=[CH:12][N:11]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C(O)(C(F)(F)F)=O>ClCCl>[N:1]1([CH2:7][CH2:8][NH:9][C:10]2[N:15]=[C:14]3[NH:16][N:17]=[C:18]([C:19]4[CH:24]=[CH:23][CH:22]=[C:21]([NH:25][CH2:26][C:27]5[S:28][CH:29]=[CH:30][CH:31]=5)[CH:20]=4)[C:13]3=[CH:12][N:11]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68108959HCID 68108959, compound

Product 1

HCID 178420614HCID 178420614, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (2-morpholin-4-yl-ethyl)-[3-{3-[(thiophen-2-ylmethyl)-amino]-phenyl}-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-d]pyrimidin-6-yl]-amine (170 mg, 0.3 mmol) in dichloromethane (10 mL) was added TFA (10 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 dissolved in EtOAc (10 mL). The organic phase was washed with saturated aqueous NaHCO3 (3 mL), brine (5 mL) and dried over anhydrous Na2SO4, filtered and concentrated. It was purified by prep-HPLC to give (2-morpholin-4-yl-ethyl)-(3-{3-[(thiophen-2-ylmethyl)-amino]-phenyl}-1H-pyrazolo[3,4-d]pyrimidin-6-yl)-amine as yellow solid. (Yield 20 mg, 11.7%).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. dissolutionthe residue was dissolved in EtOAc (10 mL)
  3. washThe organic phase was washed with saturated aqueous NaHCO3 (3 mL), brine (5 mL)
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customIt was purified by prep-HPLC

Sources & evidence

ORD record
ord-581abc5c7e6f46e7b750b23ef42413ea
Source dataset
uspto-grants-2013_01
Patent number
US08362023B2

Reaction notes

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