Trifluoroacetic acid → HCID 178507713, compound

HRID 1809725Notes

Reaction equation

HRID 1809725 reaction equation
C(OC(=O)[NH:7][CH:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[N:20]=[C:19]3[N:21](COCC[Si](C)(C)C)[N:22]=[C:23]([C:24]4[CH:29]=[CH:28][CH:27]=[C:26]([NH:30][CH2:31][C:32]5[S:33][CH:34]=[CH:35][CH:36]=5)[CH:25]=4)[C:18]3=[CH:17][N:16]=2)[CH2:10][CH2:9]1)(C)(C)C.C(O)(C(F)(F)F)=O>ClCCl>[S:33]1[CH:34]=[CH:35][CH:36]=[C:32]1[CH2:31][NH:30][C:26]1[CH:25]=[C:24]([C:23]2[C:18]3[C:19](=[N:20][C:15]([NH:14][CH:11]4[CH2:12][CH2:13][CH:8]([NH2:7])[CH2:9][CH2:10]4)=[N:16][CH:17]=3)[NH:21][N:22]=2)[CH:29]=[CH:28][CH:27]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68109008{4-[3-{3-[(thiophen-2-ylmethyl)-amino]-phenyl}-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino]-cyclohexyl}-carbamic acid tert-butyl ester

Product 1

HCID 178507713HCID 178507713, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of {4-[3-{3-[(thiophen-2-ylmethyl)-amino]-phenyl}-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino]-cyclohexyl}-carbamic acid tert-butyl ester (290 mg, 0.44 mmol) in dichloromethane (10 mL) was added TFA (15 mL) at room temperature. The resulting mixture was stirred for another four hours at this temperature. The solvent was evaporated under reduced pressure and the residue was treated with saturated aqueous NaHCO3 (5 mL) and extracted with EtOAc (30 mL). The organic phase was washed with brine (5 mL) and dried to give crude product. It was purified by chromatography (silica gel, 200-300 mesh, MeOH.:DMC, 1:20, v/v) to give N-(3-{3-[(thiophen-2-ylmethyl)-amino]-phenyl}-1H-pyrazolo[3,4-d]pyrimidin-6-yl)-cyclohexane-1,4-diamine as solid. (Yield 27 mg, 14.6%).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. additionthe residue was treated with saturated aqueous NaHCO3 (5 mL)
  3. extractionextracted with EtOAc (30 mL)
  4. washThe organic phase was washed with brine (5 mL)
  5. customdried
  6. customto give crude product
  7. customIt was purified by chromatography (silica gel, 200-300 mesh, MeOH

Sources & evidence

ORD record
ord-ab7e771a2f0644cb944058af4cf28ac0
Source dataset
uspto-grants-2013_01
Patent number
US08362023B2

Reaction notes

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