Trifluoroacetic acid → HCID 178420616, compound

HRID 1809738Notes

Reaction equation

HRID 1809738 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[CH:31]=[CH:30][S:29][CH:28]=5)[N: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[CH:31]=[CH:30][S:29][CH:28]=5)[N: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 68108327(2-morpholin-4-yl-ethyl)-[3-{6-[(thiophen-3-ylmethyl)-amino]-pyridin-2-yl}-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-d]pyrimidin-6-yl]-amine

Product 1

HCID 178420616HCID 178420616, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of crude (2-morpholin-4-yl-ethyl)-[3-{6-[(thiophen-3-ylmethyl)-amino]-pyridin-2-yl}-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-d]pyrimidin-6-yl]-amine (149 mg, crude) in dichloromethane (2 mL) was added CF3COOH (2 mL). This mixture was stirred at room temperature for 2 hours. The solvent was removed under reduced pressure. A saturated aqueous solution of NaHCO3 was added to the residue, and then extracted with ethyl acetate (3×15 mL). The combined organic phase was dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. The residue was washed with dichloromethane (2 mL) to give (2-morpholin-4-yl-ethyl)-(3-{6-[(thiophen-3-ylmethyl)-amino]-pyridin-2-yl}-1H-pyrazolo[3,4-d]pyrimidin-6-yl)-amine as a white solid. (Yield 46 mg, 18% over two steps).

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionA saturated aqueous solution of NaHCO3 was added to the residue
  3. extractionextracted with ethyl acetate (3×15 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 dichloromethane (2 mL)

Sources & evidence

ORD record
ord-07d1b977546b44a88f1e5121b3abc25e
Source dataset
uspto-grants-2013_01
Patent number
US08362023B2

Reaction notes

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