Trifluoroacetic acid → HCID 53262622, compound

HRID 1509304Notes

Reaction equation

HRID 1509304 reaction equation
[C:1]1([C:7]2[C:25]([C:26]3[CH:31]=[CH:30][C:29]([C:32]4([NH:36]C(=O)OC(C)(C)C)[CH2:35][CH2:34][CH2:33]4)=[CH:28][CH:27]=3)=[N:24][C:10]3[O:11][CH2:12][C:13]4[N:14]([C:15]([C:18]5[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=5)=[N:16][N:17]=4)[C:9]=3[CH: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[C:25]([C:26]3[CH:27]=[CH:28][C:29]([C:32]4([NH2:36])[CH2:35][CH2:34][CH2:33]4)=[CH:30][CH:31]=3)=[N:24][C:10]3[O:11][CH2:12][C:13]4[N:14]([C:15]([C:18]5[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=5)=[N:16][N:17]=4)[C:9]=3[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86683658HCID 86683658, compound

Product 1

HCID 53262622HCID 53262622, compoundYield 65.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Tert-butyl (1-(4-(8-phenyl-1-(pyridin-2-yl)-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-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. The resulting residue was purified via preparative HPLC to give the desired product as a white solid (8 mg, 64% yield). LCMS (Method D) RT=0.825 min, M+H+=474. 1H NMR (500 MHz, d6-DMSO): 8.79 (1H, d), 8.44 (1H, bs), 8.13 (1H, s), 8.11-8.05 (1H, m), 7.62-7.59 (1H, m), 7.41 (2H, s), 7.42-7.38 (2H, d), 7.25-7.27 (3H, m), 7.10 (2H, m), 5.71 (2H, s), 2.60-2.51 (4H, m), 2.27-2.19 (1H, m), 1.88-1.76 (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. customThe resulting residue was purified via preparative HPLC

Sources & evidence

ORD record
ord-7396a3c4a74841b391c6232dce33de61
Source dataset
uspto-grants-2015_12
Patent number
US09221838B2

Reaction notes

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