HCID 86683580, compound → HCID 53262118, compound

HRID 1509157Notes

Reaction equation

HRID 1509157 reaction equation
C(OC([NH:8][C:9]1([C:13]2[CH:18]=[CH:17][C:16]([C:19]3[C:20]([C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)=[CH:21][C:22]4[N:27]([CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])[C:26](=[O:34])[CH2:25][O:24][C:23]=4[N:35]=3)=[CH:15][CH:14]=2)[CH2:12][CH2:11][CH2:10]1)=O)(C)(C)C>C(O)(C(F)(F)F)=O>[NH2:8][C:9]1([C:13]2[CH:14]=[CH:15][C:16]([C:19]3[C:20]([C:36]4[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=4)=[CH:21][C:22]4[N:27]([CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])[C:26](=[O:34])[CH2:25][O:24][C:23]=4[N:35]=3)=[CH:17][CH:18]=2)[CH2:10][CH2:11][CH2:12]1

Participants

3

Reactant 1

HCID 86683580HCID 86683580, compound

Product 1

HCID 53262118HCID 53262118, compoundYield 123.3%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Ethyl 2-(6-(4-(1-(tert-butoxycarbonylamino)cyclobutyl)phenyl)-2-oxo-7-phenyl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-1-yl)acetate (22 mg, 0.039 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 by freeze drying overnight to give the desired compound as an off-white solid (22 mg, 98% yield).

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 by freeze
  6. customdrying overnight

Sources & evidence

ORD record
ord-4417710596374677ab334d942f414a6e
Source dataset
uspto-grants-2015_12
Patent number
US09221838B2

Reaction notes

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