HCID 178452588, compound → HCID 178423072, compound

HRID 1509101Notes

Reaction equation

HRID 1509101 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][CH:36]=[C:23]5[C:22]([CH3:38])([CH3:37])[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>[CH3:37][C:22]1([CH3:38])[CH2:21][C:20]2[N:19]=[C:18]([C:15]3[CH:14]=[CH:13][C:12]([C:8]4([NH2:7])[CH2:9][CH2:10][CH2:11]4)=[CH:17][CH:16]=3)[C:27]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[CH:26][C:25]=2[C:24]2=[N:34][NH:35][CH:36]=[C:23]12

Participants

3

Reactant 1

HCID 178452588HCID 178452588, compound

Product 1

HCID 178423072HCID 178423072, compoundYield 63.4%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

tert-butyl(1-(4-(4,4-dimethyl-8-phenyl-4,5-dihydro-2H-pyrazolo[3,4-f]quinolin-7-yl)phenyl)cyclobutyl)carbamate (8 mg, 0.015 mmol) was dissolved in TFA (0.5 mL) and stirred for 30 seconds. The solution was immediately concentrated to dryness under reduced pressure. The residue was dissolved in diethyl ether (˜1 mL) and concentrated to dryness under reduced pressure three times. The residue was then slurried in diethyl ether (1 mL) and after settling the supernatant solvent removed by pipette. This was repeated three times. The remaining solvent was removed under reduced pressure and dried to give the desired product as an off-white solid (4 mg, 50% yield). 1H NMR (500 MHz, CH3OD) 8.18 (s, 1H), 7.63 (s, 1H), 7.47 (d, 2H), 7.41 (d, 2H), 7.19-7.33 (br m, 5H), 3.08 (s, 2H), 2.68-2.79 (br m, 2H), 2.51-2.64 (br m, 2H), 2.15-2.30 (br m, 1H), 1.87-2.01 (br m, 1H), 1.35 (s, 6H). LCMS (Method A): RT=3.03 min, M+H+=421.

Workup

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

Sources & evidence

ORD record
ord-5583ca0c388446c38d21cb009d5c2e84
Source dataset
uspto-grants-2015_12
Patent number
US09221838B2

Reaction notes

Loading…