Trifluoroacetic acid → HCID 178511114, compound

HRID 1809756Notes

Reaction equation

HRID 1809756 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)[CH: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>ClCCl>[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[CH: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

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68108958HCID 68108958, compound

Product 1

HCID 178511114HCID 178511114, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of crude (3-{3-[6-(2-morpholin-4-yl-ethylamino)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-d]pyrimidin-3-yl]-phenylamino}-3-phenyl-propyl)-carbamic acid tert-butyl ester (329 mg, crude) in dichloromethane (1.5 mL) was added TFA (1.5 mL) at room temperature. The resulting mixture was stirred for 2 hours at room temperature. The reaction solution was concentrated under reduced pressure and partitioned between saturated NaHCO3 solution and ethyl acetate. The water phase was extracted with ethyl acetate again. The combined organic phase was dried over anhydrous Na2SO4, filtered and concentrated. The residue was purified by column chromatography (silica gel, MeOH:dichloromethane, 1:100 to 1:10). The obtained solid was dissolved in a solution of HCl in MeOH and concentrated to give N1-{3-[6-(2-morpholin-4-yl-ethylamino)-1H-pyrazolo[3,4-d]pyrimidin-3-yl]-phenyl}-1-phenyl-propane-1,3-diamine; hydrochloride. (Yield 20 mg).

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. custompartitioned between saturated NaHCO3 solution and ethyl acetate
  3. extractionThe water phase was extracted with ethyl acetate again
  4. dry with materialThe combined organic phase was dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography (silica gel, MeOH:dichloromethane, 1:100 to 1:10)
  8. dissolutionThe obtained solid was dissolved in a solution of HCl in MeOH
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-37b3ed5a28e14d9a975451f07e16bac3
Source dataset
uspto-grants-2013_01
Patent number
US08362023B2

Reaction notes

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