HCID 178503590, compound → HCID 178503589, compound

HRID 1509083Notes

Reaction equation

HRID 1509083 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][CH3:38])=[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>[CH3:38][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

Participants

3

Reactant 1

HCID 178503590HCID 178503590, compound

Product 1

HCID 178503589HCID 178503589, compoundYield 55.8%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

tert-butyl(1-(4-(3-(methylthio)-8-phenyl-4,5-dihydro-2H-pyrazolo[3,4-f]quinolin-7-yl)phenyl)cyclobutyl)carbamate (53 mg, 0.098 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 (24 mg, 37% yield). 1H-NMR (500 MHz, CD3OD) δ 8.14 (1H, br s), 7.48 (2H, d), 7.43 (2H, d), 7.27-7.34 (3H, m), 7.21-7.27 (2H, m), 3.26 (2H, t), 2.97 (2H, br t), 2.72-2.82 (2H, m), 2.53-2.63 (2H, m), 2.49 (3H, s), 2.19-2.30 (1H, m), 1.91-2.02 (1H, m). LCMS (Method A) RT=4.06 min, M+H+=439.14.

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-9aeadd815ee647d38606cbfd2b0b6c2b
Source dataset
uspto-grants-2015_12
Patent number
US09221838B2

Reaction notes

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