HCID 123476701, compound → HCID 53261798, compound

HRID 1509084Notes

Reaction equation

HRID 1509084 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]([S:37]([CH3:40])(=[O:39])=[O:38])=[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>[CH3:40][S:37]([C:36]1[NH:35][N:34]=[C:24]2[C:23]=1[CH2:22][CH2:21][C:20]1[N:19]=[C:18]([C:15]3[CH:16]=[CH:17][C:12]([C:8]4([NH2:7])[CH2:9][CH2:10][CH2:11]4)=[CH:13][CH:14]=3)[C:27]([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)=[CH:26][C:25]2=1)(=[O:38])=[O:39]

Participants

3

Reactant 1

HCID 123476701HCID 123476701, compound

Product 1

HCID 53261798HCID 53261798, compoundYield 54.6%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

tert-butyl(1-(4-(3-(methylsulfonyl)-8-phenyl-4,5-dihydro-2H-pyrazolo[3,4-f]quinolin-7-yl)phenyl)cyclobutyl)carbamate (40 mg, 0.070 mmol) was dissolved in TFA (2 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 (18 mg, 37% yield). 1H-NMR (500 MHz, CD3OD) δ 8.10 (1H, s), 7.50 (2H, d), 7.44 (2H, d), 7.31-7.35 (3H, m), 7.24-7.29 (2H, m), 3.32 (2H, t), 3.28 (3H, s), 3.24 (2H, t), 2.74-2.82 (2H, m), 2.54-2.64 (2H, m), 2.19-2.30 (1H, m), 1.92-2.03 (1H, m). LCMS (Method A) RT=3.81 min, M+H+=471.16.

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-9bbf50bcd20f4efdab7175658268c8c5
Source dataset
uspto-grants-2015_12
Patent number
US09221838B2

Reaction notes

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