HCID 86683523, compound → HCID 75995610, compound

HRID 1509071Notes

Reaction equation

HRID 1509071 reaction equation
[OH:1][N:2]=[C:3]1[CH2:12][CH2:11][CH2:10][C:9]2[N:8]=[C:7]([C:13]3[CH:18]=[CH:17][C:16]([C:19]4([NH:23]C(=O)OC(C)(C)C)[CH2:22][CH2:21][CH2:20]4)=[CH:15][CH:14]=3)[C:6]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[CH:5][C:4]1=2>C(O)(C(F)(F)F)=O>[NH2:23][C:19]1([C:16]2[CH:15]=[CH:14][C:13]([C:7]3[C:6]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)=[CH:5][C:4]4[C:3](=[N:2][OH:1])[CH2:12][CH2:11][CH2:10][C:9]=4[N:8]=3)=[CH:18][CH:17]=2)[CH2:22][CH2:21][CH2:20]1

Participants

3

Reactant 1

HCID 86683523HCID 86683523, compound

Product 1

HCID 75995610HCID 75995610, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Tert-butyl (1-(4-(5-(hydroxyimino)-3-phenyl-5,6,7,8-tetrahydroquinolin-2-yl)phenyl)cyclobutyl)carbamate (7 mg, 0.017 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 dried to give the desired product as an off-white solid (3 mg, 35% yield). 1H NMR (500 MHz, CH3OD) 8.45 (s, 1H), 7.46 (m, 5H), 7.34 (d, 2H), 7.21 (d, 2H), 3.10 (t, 2H), 2.90 (t, 2H), 2.74-2.78 (m, 2H), 2.56-2.6 (m, 2H), 2.20-2.28 (m, 1H), 2.02-2.10 (m, 2H), 1.93-1.98 (m, 1H).

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. customdried

Sources & evidence

ORD record
ord-5a9554dce6764a6dbe33ab84f4441800
Source dataset
uspto-grants-2015_12
Patent number
US09221838B2

Reaction notes

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