HCID 178452590, compound → HCID 178507124, compound

HRID 1509087Notes

Reaction equation

HRID 1509087 reaction equation
C(OC(=O)[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:27]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)=[CH:26][C:25]4[C:24]5=[N:34][NH:35][C:36]([NH:37][CH2:38][CH2:39][OH:40])=[C:23]5[CH2:22][CH2:21][C:20]=4[N:19]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)(C)(C)C>C(O)(C(F)(F)F)=O>[NH2:7][C:8]1([C:12]2[CH:13]=[CH:14][C:15]([C:18]3[C:27]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)=[CH:26][C:25]4[C:24]5=[N:34][NH:35][C:36]([NH:37][CH2:38][CH2:39][OH:40])=[C:23]5[CH2:22][CH2:21][C:20]=4[N:19]=3)=[CH:16][CH:17]=2)[CH2:11][CH2:10][CH2:9]1

Participants

3

Reactant 1

HCID 178452590HCID 178452590, compound

Product 1

HCID 178507124HCID 178507124, compoundYield 108.3%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

tert-butyl(1-(4-(3-((2-hydroxyethyl)amino)-8-phenyl-4,5-dihydro-2H-pyrazolo[3,4-f]quinolin-7-yl)phenyl)cyclobutyl)carbamate (25 mg, 0.045 mmol) was dissolved in TFA (1 mL) and stirred for 30 seconds. The solution was immediately concentrated to dryness under reduced pressure. The residue was dissolved in diethyl ether (˜2 mL) and concentrated to dryness under reduced pressure three times. The residue was then slurried in diethyl ether (2 mL) and after settling the supernatant solvent removed by pipette. This was repeated three times. The remaining solvent was removed under reduced pressure and freeze-dried to give the desired product as an off-white solid (22 mg, 71% yield). 1H-NMR (500 MHz, CD3OD) δ 8.06 (1H, s), 7.50 (2H, d), 7.44 (2H, d), 7.29-7.34 (3H, m), 7.22-7.28 (2H, m), 3.78 (2H, t), 3.41 (2H, t), 3.30 (2H, t), 2.90 (2H, t), 2.71-2.82 (2H, m), 2.54-2.66 (2H, m), 2.19-2.30 (1H, m), 1.91-2.03 (1H, m). LCMS (Method A) RT=3.30 min, M+H+=452.17.

Workup

  1. concentrationThe solution was immediately concentrated to dryness under reduced pressure
  2. dissolutionThe residue was dissolved in diethyl ether (˜2 mL)
  3. concentrationconcentrated to dryness under reduced pressure three times
  4. customremoved by pipette
  5. customThe remaining solvent was removed under reduced pressure
  6. customfreeze-dried

Sources & evidence

ORD record
ord-0bcdf24c872c457e8473ca5396b859f7
Source dataset
uspto-grants-2015_12
Patent number
US09221838B2

Reaction notes

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