HCID 67993162, compound → HCID 67993074, compound

HRID 244277Notes

Reaction equation

HRID 244277 reaction equation
[CH3:1][C:2]1[CH:22]=[CH:21][C:5]([C:6]([CH:8]2[CH2:13][CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10][CH2:9]2)=[O:7])=[CH:4][N:3]=1>C(Cl)Cl.C(O)(C(F)(F)F)=O>[CH3:1][C:2]1[N:3]=[CH:4][C:5]([C:6]([CH:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[O:7])=[CH:21][CH:22]=1

Participants

4

Reactant 1

HCID 67993162HCID 67993162, compound

Product 1

HCID 67993074HCID 67993074, compoundYield 70.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of 9a (0.7 g, 2.3 mmol) in CH2Cl2 (15 mL), TFA (2 mL) was added. The reaction mixture was stirred at room temperature for 4 h. The solvent was removed under reduced pressure and the residue was neutralized with aqueous NaOH solution and extracted with CH2Cl2 (2×15 mL). The organic layer was washed with brine, dried and concentrated to give the crude product. The crude product was purified with column chromatography to afforded 10a (0.33 g, 70%). 1H NMR (CDCl3): δ 1.62-1.87 (m, 6H), 2.63 (s, 3H), 2.77 (m, 2H), 3.16-3.22 (m, 2H), 3.33 (m, 1H), 7.27 (d, J=8.4 Hz, 1H), 8.12 (dd, J=8.1, 2.4 Hz, 1H), 9.04 (d, J=2.4 Hz, 1H).

Workup

  1. customThe solvent was removed under reduced pressure
  2. extractionextracted with CH2Cl2 (2×15 mL)
  3. washThe organic layer was washed with brine
  4. customdried
  5. concentrationconcentrated
  6. customto give the crude product
  7. customThe crude product was purified with column chromatography

Sources & evidence

ORD record
ord-7b37dcdf4d0742f3b6fa66dbe18d4092
Source dataset
uspto-grants-2014_02
Patent number
US08658131B2

Reaction notes

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