HCID 86683647, compound → HCID 53262564, compound

HRID 1509267Notes

Reaction equation

HRID 1509267 reaction equation
[CH:1]1([C:4]2[N:8]3[C:9]4[CH:16]=[C:15]([C:17]5[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=5)[C:14]([C:23]5[CH:28]=[CH:27][C:26]([C:29]6([NH:33]C(=O)OC(C)(C)C)[CH2:32][CH2:31][CH2:30]6)=[CH:25][CH:24]=5)=[N:13][C:10]=4[O:11][CH2:12][C:7]3=[N:6][N:5]=2)[CH2:3][CH2:2]1>C(O)(C(F)(F)F)=O>[CH:1]1([C:4]2[N:8]3[C:9]4[CH:16]=[C:15]([C:17]5[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=5)[C:14]([C:23]5[CH:24]=[CH:25][C:26]([C:29]6([NH2:33])[CH2:30][CH2:31][CH2:32]6)=[CH:27][CH:28]=5)=[N:13][C:10]=4[O:11][CH2:12][C:7]3=[N:6][N:5]=2)[CH2:2][CH2:3]1

Participants

3

Reactant 1

HCID 86683647HCID 86683647, compound

Product 1

HCID 53262564HCID 53262564, compoundYield 459.2%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Tert-butyl (1-(4-(1-cyclopropyl-8-phenyl-4H-pyrido[2,3-b][1,2,4]triazolo[4,3-d][1,4]oxazin-7-yl)phenyl)cyclobutyl)carbamate (36 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 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 (24 mg, 82% yield). LCMS (Method D) RT=0.747 min, M+1=436. 1H-NMR (500 MHz, CD3OD) δ 8.48 (1H, s), 7.53-7.47 (2H, m), 7.45-7.41 (2H, d), 7.38-7.33 (3H, m), 7.32-7.26 (2H, m), 5.66 (2H, s), 2.82-2.72 (2H, m), 2.63-2.55 (2H, m), 2.44-2.36 (1H, m), 2.30-2.19 (1H, m), 2.01-1.92 (1H, m), 1.28-1.17 (4H, overlapped ddd).

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 three times
  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-26f1c73cdcaa45198bd8e471b2697139
Source dataset
uspto-grants-2015_12
Patent number
US09221838B2

Reaction notes

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