Trifluoroacetic acid → HCID 53262619, compound

HRID 1509286Notes

Reaction equation

HRID 1509286 reaction equation
[F:1][CH2:2][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>ClCCl>[F:1][CH2:2][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:23]=[CH:24][C:25]([C:28]5([NH2:32])[CH2:31][CH2:30][CH2:29]5)=[CH:26][CH:27]=4)=[N:12][C:9]=3[O:10][CH2:11][C:6]2=[N:5][N:4]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86683656HCID 86683656, compound

Product 1

HCID 53262619HCID 53262619, compoundYield 61.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Tert-butyl (1-(4-(1-(fluoromethyl)-8-phenyl-4H-pyrido[2,3-b][1,2,4]triazolo[4,3-d][1,4]oxazin-7-yl)phenyl)cyclobutyl)carbamate (3 mg, 5.69 μmol) was dissolved in dichloromethane (1 ml); TFA (0.5 ml) was added at room temperature and the resulting 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-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 dried to give the desired product as an off-white solid (1.5 mg, 61% yield). LCMS (Method D) RT=0.774 min, M+1=428. 1H-NMR (500 MHz, CD3OD) δ 8.03 (1H, s), 7.41-7.35 (2H, d), 7.34-7.29 (2H, d), 7.27-7.23 (3H, m), 7.21-7.15 (2H, m), 5.86 (1H, s), 5.75 (1H, s), 5.64 (2H, s), 2.71-2.58 (2H, m), 2.49-2.37 (2H, m), 2.18-2.07 (1H, m), 1.91-1.79 (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-85a30e14c5ee4d309f73096e2b6099c1
Source dataset
uspto-grants-2015_12
Patent number
US09221838B2

Reaction notes

Loading…