Trifluoroacetic acid → HCID 178478137, compound

HRID 1809720Notes

Reaction equation

HRID 1809720 reaction equation
[Cl:1][C:2]1[CH:41]=[CH:40][C:5]([CH2:6][NH:7][C:8]2[N:13]=[C:12]([C:14]3[C:22]4[C:17](=[N:18][C:19]([NH:23][CH2:24][CH2:25][N:26]5[CH2:31][CH2:30][O:29][CH2:28][CH2:27]5)=[N:20][CH:21]=4)[N:16](COCC[Si](C)(C)C)[N:15]=3)[CH:11]=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O.C([O-])(O)=O.[Na+]>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][NH:7][C:8]2[N:13]=[C:12]([C:14]3[C:22]4[C:17](=[N:18][C:19]([NH:23][CH2:24][CH2:25][N:26]5[CH2:27][CH2:28][O:29][CH2:30][CH2:31]5)=[N:20][CH:21]=4)[NH:16][N:15]=3)[CH:11]=[CH:10][CH:9]=2)=[CH:40][CH:41]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 68108794[3-[6-(4-chloro-benzylamino)-pyridin-2-yl]-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-d]pyrimidin-6-yl]-(2-morpholin-4-yl-ethyl)-amine

Product 1

HCID 178478137HCID 178478137, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [3-[6-(4-chloro-benzylamino)-pyridin-2-yl]-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-d]pyrimidin-6-yl]-(2-morpholin-4-yl-ethyl)-amine (100 mg, 0.168 mmol) in dichloromethane (2 mL) was added TFA (2 mL). The reaction mixture was stirred for 2 hours at room temperature. The pH of mixture was then adjusted to about 8 with saturated NaHCO3 solution. The resulting mixture was extracted with dichloromethane. The organic layer was dried and concentrated under reduced pressure. The residue was purified by prep-HPLC to give {3-[6-(4-Chloro-benzylamino)-pyridin-2-yl]-1H-pyrazolo[3,4-d]pyrimidin-6-yl}-(2-morpholin-4-yl-ethyl)-amine. (Yield 20 mg, 26%).

Workup

  1. extractionThe resulting mixture was extracted with dichloromethane
  2. customThe organic layer was dried
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by prep-HPLC

Sources & evidence

ORD record
ord-e05a1261e37942738e7975c147a7311a
Source dataset
uspto-grants-2013_01
Patent number
US08362023B2

Reaction notes

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