Trifluoroacetic acid → HCID 178507714, compound

HRID 1809735Notes

Reaction equation

HRID 1809735 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[CH:36]=[CH:35][S:34][CH:33]=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:34]1[CH:35]=[CH:36][C:32]([CH2:31][NH:30][C:26]2[CH:25]=[C:24]([C:23]3[C:18]4[C:19](=[N:20][C:15]([NH:14][CH:11]5[CH2:12][CH2:13][CH:8]([NH2:7])[CH2:9][CH2:10]5)=[N:16][CH:17]=4)[NH:21][N:22]=3)[CH:29]=[CH:28][CH:27]=2)=[CH:33]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68108908{4-[3-{3-[(thiophen-3-ylmethyl)-amino]-phenyl}-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino]-cyclohexyl}-carbamic acid tert-butyl ester

Product 1

HCID 178507714HCID 178507714, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of {4-[3-{3-[(thiophen-3-ylmethyl)-amino]-phenyl}-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino]-cyclohexyl}-carbamic acid tert-butyl ester (120 mg, 0.185 mmol) in dichloromethane (3 mL) was added TFA (3 mL) at room temperature. The resulting mixture was stirred for another two 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 prep-HPLC to give N-(3-{3-[(thiophen-3-ylmethyl)-amino]-phenyl}-1H-pyrazolo[3,4-d]pyrimidin-6-yl)-cyclohexane-1,4-diamine as solid. (Yield 75 mg, 84%).

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 prep-HPLC

Sources & evidence

ORD record
ord-6e090446b05b4ca8aca929d7e690a7af
Source dataset
uspto-grants-2013_01
Patent number
US08362023B2

Reaction notes

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