HCID 86683649, compound → HCID 53262565, compound

HRID 1509270Notes

Reaction equation

HRID 1509270 reaction equation
[CH:1]([C:4]1[N:8]2[C:9]3[CH:16]=[C:15]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[C:14]([C:23]4[CH:28]=[CH:27][C:26]([C:29]5([NH:33]C(=O)OC(C)(C)C)[CH2:32][CH2:31][CH2:30]5)=[CH:25][CH:24]=4)=[N:13][C:10]=3[O:11][CH2:12][C:7]2=[N:6][N:5]=1)([CH3:3])[CH3:2]>C(O)(C(F)(F)F)=O>[CH:1]([C:4]1[N:8]2[C:9]3[CH:16]=[C:15]([C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=4)[C:14]([C:23]4[CH:24]=[CH:25][C:26]([C:29]5([NH2:33])[CH2:30][CH2:31][CH2:32]5)=[CH:27][CH:28]=4)=[N:13][C:10]=3[O:11][CH2:12][C:7]2=[N:6][N:5]=1)([CH3:3])[CH3:2]

Participants

3

Reactant 1

HCID 86683649HCID 86683649, compound

Product 1

HCID 53262565HCID 53262565, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Tert-butyl (1-(4-(1-isopropyl-8-phenyl-4H-pyrido[2,3-b][1,2,4]triazolo[4,3-d][1,4]oxazin-7-yl)phenyl)cyclobutyl)carbamate (24 mg, 0.045 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 (18 mg, 92% yield). LCMS (Method D) RT=0.815 min, M+1=438. 1H-NMR (500 MHz, CD3OD) δ 8.18 (1H, s), 7.52-7.47 (2H, m), 7.45-7.41 (2H, d), 7.38-7.34 (3H, m), 7.31-7.26 (2H, m), 5.64 (2H, s), 2.82-2.72 (2H, m), 2.63-2.54 (2H, m), 2.30-2.19 (1H, m), 2.02-1.92 (1H, m), 1.51 (6H, d).

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-c978f03efbcb475c83a071affe17abd0
Source dataset
uspto-grants-2015_12
Patent number
US09221838B2

Reaction notes

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