Trifluoroacetic acid → HCID 53261684, compound

HRID 1509303Notes

Reaction equation

HRID 1509303 reaction equation
[C:1]1([C:7]2[N:11]3[C:12]4[CH:19]=[C:18]([C:20]5[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=5)[C:17]([C:26]5[CH:31]=[CH:30][C:29]([C:32]6([NH:36]C(=O)OC(C)(C)C)[CH2:35][CH2:34][CH2:33]6)=[CH:28][CH:27]=5)=[N:16][C:13]=4[O:14][CH2:15][C:10]3=[N:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)(C(F)(F)F)=O>ClCCl>[C:1]1([C:7]2[N:11]3[C:12]4[CH:19]=[C:18]([C:20]5[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=5)[C:17]([C:26]5[CH:27]=[CH:28][C:29]([C:32]6([NH2:36])[CH2:35][CH2:34][CH2:33]6)=[CH:30][CH:31]=5)=[N:16][C:13]=4[O:14][CH2:15][C:10]3=[N:9][N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86683668HCID 86683668, compound

Product 1

HCID 53261684HCID 53261684, compoundYield 40.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Tert-butyl (1-(4-(1,8-diphenyl-4H-pyrido[2,3-b][1,2,4]triazolo[4,3-d][1,4]oxazin-7-yl)phenyl)cyclobutyl)carbamate (15 mg, 0.026 mmol) 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-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 dried to give the desired product as an off-white solid (5 mg, 40% yield). LCMS (Method D) RT=0.846 min, M+1=472. 1H NMR (500 MHz, CDCl3): 7.91-7.86 (2H, dd), 7.83-7.76 (3H, m), 7.59-7.54 (2H, d), 7.53-7.48 (2H, d), 7.42 (1H, s), 7.37-7.28 (3H, m), 7.09-7.03 (2H, dd), 5.86 (2H, s), 2.91-2.81 (2H, m), 2.74-2.63 (2H, m), 2.40-2.29 (1H, m), 2.13-2.02 (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. customremoved by pipette
  6. customThe remaining solvent was removed under reduced pressure
  7. customdried

Sources & evidence

ORD record
ord-10d0ef697bd644e4b4e6076097e3d800
Source dataset
uspto-grants-2015_12
Patent number
US09221838B2

Reaction notes

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