HCID 86683614, compound → HCID 53262414, compound

HRID 1509219Notes

Reaction equation

HRID 1509219 reaction equation
[CH3:1][S:2]([CH2:5][N:6]1[C:11](=[O:12])[CH2:10][O:9][C:8]2[N:13]=[C:14]([C:23]3[CH:28]=[CH:27][C:26]([C:29]4([NH:33]C(=O)OC(C)(C)C)[CH2:32][CH2:31][CH2:30]4)=[CH:25][CH:24]=3)[C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:16][C:7]1=2)(=[O:4])=[O:3]>C(O)(C(F)(F)F)=O>[NH2:33][C:29]1([C:26]2[CH:27]=[CH:28][C:23]([C:14]3[C:15]([C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=4)=[CH:16][C:7]4[N:6]([CH2:5][S:2]([CH3:1])(=[O:4])=[O:3])[C:11](=[O:12])[CH2:10][O:9][C:8]=4[N:13]=3)=[CH:24][CH:25]=2)[CH2:32][CH2:31][CH2:30]1

Participants

3

Reactant 1

HCID 86683614HCID 86683614, compound

Product 1

HCID 53262414HCID 53262414, compoundYield 120.8%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

tert-Butyl 1-(4-(1-(methylsulfonylmethyl)-2-oxo-7-phenyl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-6-yl)phenyl)cyclobutylcarbamate (28 mg, 0.050 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 (˜3 mL) and concentrated to dryness under reduced pressure three times. The residue was then slurried in diethyl ether (3 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 over the weekend to give the desired product as an off-white solid (28 mg, 98% yield). 1H-NMR (500 MHz, MeOD) δ 7.78 (1H, s), 7.32 (2H, d), 7.28 (2H, d), 7.13-7.23 (3H, m), 7.08-7.13 (2H, m), 5.43 (2H, s), 5.01 (2H, s), 2.86 (3H, s), 2.58-2.70 (2H, m), 2.40-2.52 (2H, m), 2.03-2.17 (1H, m), 1.76-1.90 (1H, m). LCMS (Method D) RT=0.87 min, M+H+=464.00.

Workup

  1. concentrationThe solution was immediately concentrated to dryness under reduced pressure
  2. dissolutionThe residue was dissolved in diethyl ether (˜3 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 over the weekend

Sources & evidence

ORD record
ord-64afb03465f24f859334cc6b40777352
Source dataset
uspto-grants-2015_12
Patent number
US09221838B2

Reaction notes

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