HCID 86683594, compound → HCID 53262183, compound

HRID 1509182Notes

Reaction equation

HRID 1509182 reaction equation
[CH3:1][C:2]1[N:6]2[C:7]3[CH:14]=[C:13]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)[C:12]([C:21]4[CH:26]=[CH:25][C:24]([C:27]5([NH:31]C(=O)OC(C)(C)C)[CH2:30][CH2:29][CH2:28]5)=[CH:23][CH:22]=4)=[N:11][C:8]=3[O:9][CH2:10][C:5]2=[N:4][N:3]=1>C(O)(C(F)(F)F)=O>[CH3:1][C:2]1[N:6]2[C:7]3[CH:14]=[C:13]([C:15]4[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=4)[C:12]([C:21]4[CH:22]=[CH:23][C:24]([C:27]5([NH2:31])[CH2:30][CH2:29][CH2:28]5)=[CH:25][CH:26]=4)=[N:11][C:8]=3[O:9][CH2:10][C:5]2=[N:4][N:3]=1

Participants

3

Reactant 1

HCID 86683594HCID 86683594, compound

Product 1

HCID 53262183HCID 53262183, compoundYield 55.5%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Tert-butyl (1-(4-(1-methyl-8-phenyl-4H-pyrido[2,3-b][1,2,4]triazolo[4,3-d][1,4]oxazin-7-yl)phenyl)cyclobutyl)carbamate (11 mg, 0.022 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-hexanes (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 (5 mg, 55% yield). LCMS (Method A): RT=3.71 min, M+1=411. 1H-NMR (500 MHz, CD3OD) δ 8.11 (1H, s), 7.49-7.44 (2H, d), 7.42-7.37 (2H, d), 7.35-7.30 (3H, m), 7.29-7.25 (2H, m), 5.63 (2H, s), 2.84 (3H, s), 2.80-2.70 (2H, m), 2.61-2.51 (2H, m), 2.28-2.17 (1H, m), 2.01-1.88 (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-c60ec423afa4481d88e4df140ffd5dde
Source dataset
uspto-grants-2015_12
Patent number
US09221838B2

Reaction notes

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