HCID 86683635, compound → HCID 86683636, compound

HRID 1509248Notes

Reaction equation

HRID 1509248 reaction equation
[C:1]1([C:7]2[C:23]([C:24]3[CH:29]=[CH:28][C:27]([C:30]4([NH:34]C(=O)OC(C)(C)C)[CH2:33][CH2:32][CH2:31]4)=[CH:26][CH:25]=3)=[N:22][C:10]3[O:11][CH2:12][C:13]4[N:14]([C:15]([C:18]([F:21])([F:20])[F:19])=[N:16][N:17]=4)[C:9]=3[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C(O)(C(F)(F)F)=O>[C:1]1([C:7]2[C:23]([C:24]3[CH:25]=[CH:26][C:27]([C:30]4([NH2:34])[CH2:33][CH2:32][CH2:31]4)=[CH:28][CH:29]=3)=[N:22][C:10]3[O:11][CH2:12][C:13]4[N:14]([C:15]([C:18]([F:20])([F:19])[F:21])=[N:16][N:17]=4)[C:9]=3[CH:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

3

Reactant 1

HCID 86683635HCID 86683635, compound

Product 1

HCID 86683636HCID 86683636, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Tert-butyl (1-(4-(8-phenyl-1-(trifluoromethyl)-4H-pyrido[2,3-b][1,2,4]triazolo[4,3-d][1,4]oxazin-7-yl)phenyl)cyclobutyl)carbamate (7 mg, 0.012 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 was removed by pipette. This was repeated three times. The residue was then slurred in n-hexane (2 ml) and after settling the supernatant solvent was 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 (1.5 mg, 26% yield). LCMS (Method D): RT=0.877 min, M+1=465. 1H-NMR (500 MHz, CD3OD) δ 8.02 (1H, s), 7.50 (2H, d), 7.43 (2H, d), 7.38-7.36 (3H, m), 7.25 (2H, m), 5.77 (2H, s), 2.75-2.69 (2H, m), 2.55-2.42 (2H, m), 2.29-2.17 (1H, m), 2.05-1.90 (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. customwas removed by pipette
  5. customwas removed by pipette
  6. customThe remaining solvent was removed under reduced pressure
  7. customthe residue was dried

Sources & evidence

ORD record
ord-5f3e37a3bbd0442a8b14e396811e0813
Source dataset
uspto-grants-2015_12
Patent number
US09221838B2

Reaction notes

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