HCID 67019997, compound → HCID 25061814, compound

HRID 1673223Notes

Reaction equation

HRID 1673223 reaction equation
C([O:8][CH2:9][C:10]1([CH3:38])[O:33][C:14]2=[N:15][C:16]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[Cl:32])=[C:17]([C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=3)[CH:18]=[C:13]2[CH:12]([NH:34][C:35](=[O:37])[CH3:36])[CH2:11]1)C1C=CC=CC=1>C(Cl)Cl>[Cl:32][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=1[C:16]1[N:15]=[C:14]2[O:33][C:10]([CH2:9][OH:8])([CH3:38])[CH2:11][CH:12]([NH:34][C:35](=[O:37])[CH3:36])[C:13]2=[CH:18][C:17]=1[C:19]1[CH:20]=[CH:21][C:22]([Cl:25])=[CH:23][CH:24]=1

Participants

3

Reactant 1

HCID 67019997HCID 67019997, compound

Product 1

HCID 25061814HCID 25061814, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The product of step B (20 mg, 0.037 mmol) was dissolved in CH2Cl2 (1 mL) and FeCl3 (25 mg, 0.15 mmol) was added. The reaction was stirred at rt for 30 min and was concentrated. The residue was added to a silica gel flash chromatography column and eluted with 0-100% EtOAc in hexane. After concentration of the desired fractions the product was repurified by semi preparative reverse phase HPLC on a C18 column, eluting with 10 to 80% MeCN/H2O (each containing 0.5% TFA). The desired fractions were neutralized with a saturated solution of NaHCO3 and extracted with EtOAc. Evaporation and drying in vacuo afforded the title compound. (LC-2) HPLC/MS: 457.3 (M+1), 459.3 (M+3); Rt=3.11 min.

Workup

  1. concentrationwas concentrated
  2. additionThe residue was added to a silica gel flash chromatography column
  3. washeluted with 0-100% EtOAc in hexane
  4. customAfter concentration of the desired fractions the product was repurified by semi preparative reverse phase HPLC on a C18 column
  5. washeluting with 10 to 80% MeCN/H2O (each containing 0.5% TFA)
  6. extractionextracted with EtOAc
  7. customEvaporation
  8. customdrying in vacuo

Sources & evidence

ORD record
ord-ac90aeb227a64559bca391fa1611ecfc
Source dataset
uspto-grants-2011_08
Patent number
US07999107B2

Reaction notes

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