Trifluoroacetic acid → HCID 67256848, compound

HRID 1509297Notes

Reaction equation

HRID 1509297 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[CH2:6][O:5][C:4]2[N:9]=[C:10]([C:18]3[CH:23]=[CH:22][C:21]([C:24]4([NH:28]C(=O)OC(C)(C)C)[CH2:27][CH2:26][CH2:25]4)=[CH:20][CH:19]=3)[C:11]([C:13]3[S:14][CH:15]=[CH:16][CH:17]=3)=[CH:12][C:3]1=2.C(O)(C(F)(F)F)=O>ClCCl>[NH2:28][C:24]1([C:21]2[CH:22]=[CH:23][C:18]([C:10]3[C:11]([C:13]4[S:14][CH:15]=[CH:16][CH:17]=4)=[CH:12][C:3]4[N:2]([CH3:1])[C:7](=[O:8])[CH2:6][O:5][C:4]=4[N:9]=3)=[CH:19][CH:20]=2)[CH2:27][CH2:26][CH2:25]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86683664HCID 86683664, compound

Product 1

HCID 67256848HCID 67256848, compoundYield 149%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Tert-butyl (1-(4-(1-methyl-2-oxo-7-(thiophen-2-yl)-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-6-yl)phenyl)cyclobutyl)carbamate (12 mg, 0.024 mmol) was dissolved in dichloromethane (1.5 ml). TFA (1 ml) was added at room temperature and the reaction mixture was 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-hexanes (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 dried to give the desired product as an off-white solid (14 mg, 78% yield). LCMS (Method D): RT=0.781 min, M+1=393. 1H-NMR (500 MHz, CD3OD) δ 7.66 (1H, s), 7.53-7.49 (2H, dd), 7.48-7.44 (2H, dd), 7.42-7.39 (1H, dd), 7.01-7.97 (1H, dd), 6.97-6.95 (1H, dd), 4.97 (2H, s), 3.44 (3H, s), 2.84-2.74 (2H, m), 2.64-2.55 (2H, m), 2.31-2.21 (1H, m), 2.07-1.93 (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. customdried

Sources & evidence

ORD record
ord-d3b8b6c654e74b069b784f5cf7709f9c
Source dataset
uspto-grants-2015_12
Patent number
US09221838B2

Reaction notes

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