Trifluoroacetic acid → (2-morpholin-4-yl-ethyl)-(3-{3-[(thiophen-3-ylmethyl)-amino]-phenyl}-1H-pyrazolo[3,4-d]pyrimidin-6-yl)-amine

HRID 1809723Notes

Reaction equation

HRID 1809723 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)[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[CH:31]=[CH:30][S:29][CH:28]=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 68108621(2-morpholin-4-yl-ethyl)-[3-{3-[(thiophen-3-ylmethyl)-amino]-phenyl}-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-d]pyrimidin-6-yl]-amine

Product 1

HCID 178420615(2-morpholin-4-yl-ethyl)-(3-{3-[(thiophen-3-ylmethyl)-amino]-phenyl}-1H-pyrazolo[3,4-d]pyrimidin-6-yl)-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the stirred solution of (2-morpholin-4-yl-ethyl)-[3-{3-[(thiophen-3-ylmethyl)-amino]-phenyl}-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-d]pyrimidin-6-yl]-amine (150 mg, 0.265 mmol) in dichloromethane (3 mL) was added TFA (3 mL) at room temperature. The resulting mixture was stirred for another two hours at this temperature. The solvent was then evaporated under reduced pressure and the pH of the residue was adjusted to 8 with saturated NaHCO3. The resulting mixture was extracted with EtOAc (10 mL). The organic layer was dried and concentrated. It was purified by prep-HPLC to give (2-morpholin-4-yl-ethyl)-(3-{3-[(thiophen-3-ylmethyl)-amino]-phenyl}-1H-pyrazolo[3,4-d]pyrimidin-6-yl)-amine. (Yield 70 mg, 61%).

Workup

  1. customThe solvent was then evaporated under reduced pressure
  2. extractionThe resulting mixture was extracted with EtOAc (10 mL)
  3. customThe organic layer was dried
  4. concentrationconcentrated
  5. customIt was purified by prep-HPLC

Sources & evidence

ORD record
ord-213a5bce0d244aff9b5267c1cdc82f5d
Source dataset
uspto-grants-2013_01
Patent number
US08362023B2

Reaction notes

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