HCID 86683632, compound → HCID 68299675, compound

HRID 1509244Notes

Reaction equation

HRID 1509244 reaction equation
[F:1][CH:2]([F:40])[C:3]1[N:7]2[C:8]3[CH:15]=[C:14]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[C:13]([C:22]4[CH:27]=[CH:26][C:25]([C:28]5([NH:32]C(=O)OC(C)(C)C)[CH2:31][CH2:30][CH2:29]5)=[CH:24][CH:23]=4)=[N:12][C:9]=3[O:10][CH2:11][C:6]2=[N:5][N:4]=1>C(O)(C(F)(F)F)=O>[F:40][CH:2]([F:1])[C:3]1[N:7]2[C:8]3[CH:15]=[C:14]([C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=4)[C:13]([C:22]4[CH:27]=[CH:26][C:25]([C:28]5([NH2:32])[CH2:31][CH2:30][CH2:29]5)=[CH:24][CH:23]=4)=[N:12][C:9]=3[O:10][CH2:11][C:6]2=[N:5][N:4]=1

Participants

3

Reactant 1

HCID 86683632HCID 86683632, compound

Product 1

HCID 68299675HCID 68299675, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Tert-butyl (1-(4-(1-(difluoromethyl)-8-phenyl-4H-pyrido[2,3-b][1,2,4]triazolo[4,3-d][1,4]oxazin-7-yl)phenyl)cyclobutyl)carbamate (15 mg, 0.073 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. This was repeated three times. The residue was then slurred in diethyl ether (2 ml) and after settling the supernatant solvent removed by pipette. This was repeated three times. The residue was then slurred in n-hexane (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 the residue was dried to give the desired product as an off-white solid (8 mg, 65% yield). LCMS (Method D): RT=0.803 min, M+1=446. 1H-NMR (500 MHz, CD3OD) δ 8.20 (1H, s), 7.53-7.47 (3H, m), 7.46-7.41 (2H, m), 7.39-7.33 (3H, m), 7.30-7.23 (2H, m), 5.77 (2H, s), 2.83-2.70 (2H, m), 2.63-2.53 (2H, m), 2.30-2.19 (1H, m), 2.06-1.90 (1H, m).

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
  4. customremoved by pipette
  5. customremoved by pipette
  6. customThe remaining solvent was removed under reduced pressure
  7. customthe residue was dried

Sources & evidence

ORD record
ord-e8ee5c8a1dee491e8ccdc11c19bd0059
Source dataset
uspto-grants-2015_12
Patent number
US09221838B2

Reaction notes

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