Trifluoroacetic acid → HCID 178478038, compound

HRID 1809733Notes

Reaction equation

HRID 1809733 reaction equation
[Cl:1][C:2]1[CH:41]=[CH:40][CH:39]=[CH:38][C:3]=1[CH2:4][NH:5][C:6]1[CH:7]=[C:8]([C:12]2[C:20]3[C:15](=[N:16][C:17]([NH:21][CH2:22][CH2:23][N:24]4[CH2:29][CH2:28][O:27][CH2:26][CH2:25]4)=[N:18][CH:19]=3)[N:14](COCC[Si](C)(C)C)[N:13]=2)[CH:9]=[CH:10][CH:11]=1.C(O)(C(F)(F)F)=O>ClCCl>[Cl:1][C:2]1[CH:41]=[CH:40][CH:39]=[CH:38][C:3]=1[CH2:4][NH:5][C:6]1[CH:7]=[C:8]([C:12]2[C:20]3[C:15](=[N:16][C:17]([NH:21][CH2:22][CH2:23][N:24]4[CH2:29][CH2:28][O:27][CH2:26][CH2:25]4)=[N:18][CH:19]=3)[NH:14][N:13]=2)[CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68108071HCID 68108071, compound

Product 1

HCID 178478038HCID 178478038, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of [3-[3-(2-chloro-benzylamino)-phenyl]-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-d]pyrimidin-6-yl]-(2-morpholin-4-yl-ethyl)-amine (120 mg, 0.202 mmol) in dichloromethane (3 mL) was added TFA (3 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 pH of the residue was adjusted to 8 with saturated NaHCO3. The resulting mixture was extracted with EtOAc (10 mL), dried and concentrated. It was purified by prep-HPLC to give {3-[3-(2-chloro-benzylamino)-phenyl]-1H-pyrazolo[3,4-d]pyrimidin-6-yl}-(2-morpholin-4-yl-ethyl)-amine. (Yield 15 mg, 61%).

Workup

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

Sources & evidence

ORD record
ord-e5837b7b87b74401b4f6eaf18a5fd178
Source dataset
uspto-grants-2013_01
Patent number
US08362023B2

Reaction notes

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