Trifluoroacetic acid → {3-[6-(3-chloro-benzylamino)-pyridin-2-yl]-1H-pyrazolo[3,4-d]pyrimidin-6-yl}-(2-morpholin-4-yl-ethyl)-amine

HRID 1809718Notes

Reaction equation

HRID 1809718 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:39]=[CH:40][CH:41]=1)[CH2:5][NH:6][C:7]1[N:12]=[C:11]([C:13]2[C:21]3[C:16](=[N:17][C:18]([NH:22][CH2:23][CH2:24][N:25]4[CH2:30][CH2:29][O:28][CH2:27][CH2:26]4)=[N:19][CH:20]=3)[N:15](COCC[Si](C)(C)C)[N:14]=2)[CH:10]=[CH:9][CH:8]=1.C(O)(C(F)(F)F)=O.C([O-])(O)=O.[Na+]>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:39]=[CH:40][CH:41]=1)[CH2:5][NH:6][C:7]1[N:12]=[C:11]([C:13]2[C:21]3[C:16](=[N:17][C:18]([NH:22][CH2:23][CH2:24][N:25]4[CH2:26][CH2:27][O:28][CH2:29][CH2:30]4)=[N:19][CH:20]=3)[NH:15][N:14]=2)[CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 68108833HCID 68108833, compound

Product 1

HCID 178478111{3-[6-(3-chloro-benzylamino)-pyridin-2-yl]-1H-pyrazolo[3,4-d]pyrimidin-6-yl}-(2-morpholin-4-yl-ethyl)-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [3-[6-(3-chloro-benzylamino)-pyridin-2-yl]-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-d]pyrimidin-6-yl]-(2-morpholin-4-yl-ethyl)-amine (110 mg, 0.185 mmol) in dichloromethane (2.5 mL) was added TFA (2.5 mL). The reaction mixture was stirred for 2 hours at room temperature. The pH of the mixture was adjusted to about 8 with saturated NaHCO3 solution. The resulting mixture was extracted with ethyl acetate. The organic layer was dried and concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, dichloromethane:MeOH, 20:1), then further purified by prep-HPLC to give {3-[6-(3-chloro-benzylamino)-pyridin-2-yl]-1H-pyrazolo[3,4-d]pyrimidin-6-yl}-(2-morpholin-4-yl-ethyl)-amine. (Yield 23 mg, 26%).

Workup

  1. extractionThe resulting mixture was extracted with ethyl acetate
  2. customThe organic layer was dried
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by column chromatography (silica gel, dichloromethane:MeOH, 20:1)
  5. customfurther purified by prep-HPLC

Sources & evidence

ORD record
ord-daa07fe3b0464c7195a201aa0d669bf3
Source dataset
uspto-grants-2013_01
Patent number
US08362023B2

Reaction notes

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