HCID 68108371, compound → HCID 178511115, compound

HRID 1809760Notes

Reaction equation

HRID 1809760 reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][CH:10]([NH:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([C:24]2[C:32]3[C:27](=[N:28][C:29]([NH:33][CH2:34][CH2:35][N:36]4[CH2:41][CH2:40][O:39][CH2:38][CH2:37]4)=[N:30][CH:31]=3)[N:26](COCC[Si](C)(C)C)[N:25]=2)[N:19]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(C)(C)C>C(O)(C(F)(F)F)=O>[N:36]1([CH2:35][CH2:34][NH:33][C:29]2[N:28]=[C:27]3[NH:26][N:25]=[C:24]([C:20]4[N:19]=[C:18]([NH:17][CH:10]([C:11]5[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=5)[CH2:9][CH2:8][NH2:7])[CH:23]=[CH:22][CH:21]=4)[C:32]3=[CH:31][N:30]=2)[CH2:41][CH2:40][O:39][CH2:38][CH2:37]1

Participants

3

Reactant 1

HCID 68108371HCID 68108371, compound

Product 1

HCID 178511115HCID 178511115, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

(3-{6-[6-(2-Morpholin-4-yl-ethylamino)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-d]pyrimidin-3-yl]-pyridin-2-ylamino}-3-phenyl-propyl)-carbamic acid tert-butyl ester (147 mg, 0.209 mmol) was dissolved in CF3COOH (4 mL). The mixture was heated at reflux for 15 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 Na2SO4, filtered and concentrated under reduced pressure. After purification by prep-HPLC, concentrated HCl was added to the fractions with product and concentrated under reduced pressure to give N1-{6-[6-(2-Morpholin-4-yl-ethylamino)-1H-pyrazolo[3,4-d]pyrimidin-3-yl]-pyridin-2-yl}-1-phenyl-propane-1,3-diamine; hydrochloride as a yellow solid. (Yield 16 mg, 16.2%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 15 hours
  3. customThe solvent was removed under reduced pressure
  4. additionA saturated aqueous solution of NaHCO3 was added to the residue
  5. extractionextracted with ethyl acetate (3×15 mL)
  6. dry with materialThe combined organic phase was dried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customAfter purification by prep-HPLC, concentrated HCl
  10. additionwas added to the fractions with product
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7e814df853fb4d3dbc7e16456efba0de
Source dataset
uspto-grants-2013_01
Patent number
US08362023B2

Reaction notes

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