HCID 86683661, compound → HCID 53262621, compound

HRID 1509295Notes

Reaction equation

HRID 1509295 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[CH2:6][O:5][C:4]2[N:9]=[C:10]([C:19]3[CH:24]=[CH:23][C:22]([C:25]4([NH:29]C(=O)OC(C)(C)C)[CH2:28][CH2:27][CH2:26]4)=[CH:21][CH:20]=3)[C:11]([C:13]3[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=3)=[CH:12][C:3]1=2>C(O)(C(F)(F)F)=O>[NH2:29][C:25]1([C:22]2[CH:23]=[CH:24][C:19]([C:10]3[C:11]([C:13]4[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=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:20][CH:21]=2)[CH2:28][CH2:27][CH2:26]1

Participants

3

Reactant 1

HCID 86683661HCID 86683661, compound

Product 1

HCID 53262621HCID 53262621, compoundYield 144.9%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Tert-butyl (1-(4-(1-methyl-2-oxo-7-(pyridin-3-yl)-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-6-yl)phenyl)cyclobutyl)carbamate (12 mg, 0.025 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-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=0.546 min, M+1=387. 1H-NMR (500 MHz, CD3OD) δ 8.57-8.49 (1H, br s), 8.45-8.36 (1H, br s), 7.90 (1H, d), 7.67 (1H, s), 7.61-7.48 (2H, d), 7.48-7.36 (4H, m), 5.00 (2H, s), 3.45 (3H, s), 2.84-2.72 (2H, m), 2.65-2.54 (2H, m), 2.32-2.16 (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. 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-901c6589b6894f8c85e9799855e53f26
Source dataset
uspto-grants-2015_12
Patent number
US09221838B2

Reaction notes

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