Trifluoroacetic acid → HCID 86679000, compound

HRID 2203364Notes

Reaction equation

HRID 2203364 reaction equation
[NH2:1][C:2]1[C:3]2[C:28]([NH:30]C(=O)OC(C)(C)C)([CH3:29])[C:27](=[O:38])[NH:26][C:4]=2[N:5]=[C:6]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[CH:14][CH:15]=3)[N:10]([CH2:17][CH2:18][C:19]([F:25])([F:24])[C:20]([F:23])([F:22])[F:21])[N:9]=2)[N:7]=1.FC(F)(F)C(O)=O>C(Cl)Cl.CCOC(C)=O>[NH2:1][C:2]1[C:3]2[C:28]([NH2:30])([CH3:29])[C:27](=[O:38])[NH:26][C:4]=2[N:5]=[C:6]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[CH:14][CH:15]=3)[N:10]([CH2:17][CH2:18][C:19]([F:25])([F:24])[C:20]([F:21])([F:23])[F:22])[N:9]=2)[N:7]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86679001HCID 86679001, compound

Product 1

HCID 86679000HCID 86679000, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

The intermediate from Step A (111 mg, 0.205 mmol) was dissolved in DCM (2.0 mL) and trifluoroacetic acid (0.39 mL, 5.12 mmol). The solution was stirred overnight at room temperature. The reaction was then diluted with EtOAc and washed with 1N NaOH aq. (twice) and brine. The solution was then dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography using a MeOH/EtOAc gradient to give the indicated product. m/z=443.1 (M+H).

Workup

  1. washwashed with 1N NaOH aq. (twice) and brine
  2. dry with materialThe solution was then dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel column chromatography
  6. customto give the indicated product

Sources & evidence

ORD record
ord-a1d63d8b18a146d588cd0ee8e3109ec0
Source dataset
uspto-grants-2016_06
Patent number
US09365574B2

Reaction notes

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