Formic Acid → HCID 59161186, compound

HRID 545576Notes

Reaction equation

HRID 545576 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:13](=[CH:14][CH:15]=1)[N:12]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[CH:18]=1)[C:11]1[CH2:10][CH2:9][C@@H:8]([NH:24][C:25](=[O:29])[CH:26]([CH3:28])[CH3:27])[CH2:7][C:6]2=1)#N.C(O)=[O:31]>O.CO>[F:23][C:19]1[CH:18]=[C:17]([CH:22]=[CH:21][CH:20]=1)[CH2:16][N:12]1[C:11]2[CH2:10][CH2:9][C@@H:8]([NH:24][C:25](=[O:29])[CH:26]([CH3:27])[CH3:28])[CH2:7][C:6]=2[C:5]2[C:13]1=[CH:14][CH:15]=[C:3]([CH:1]=[O:31])[CH:4]=2

Participants

5

Reactant 2

HCID 284Formic AcidHCID 59161298HCID 59161298, compound

Product 1

HCID 59161186HCID 59161186, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

Add Al—Ni catalyst [12635-27-7] (3.0 g) to a solution of (R)-N-(6cyano9-(3-fluorobenzyl)-2,3,4,9-tetrahydro-1H-carbazol-3-yl)isobutyramide (Example 123) (2.50 g, 6.42 mmol) in formic acid (96%, 40 mL) and water (5 mL). Heat the reaction mixture to 90° C. for 18 h, then add 2 g fresh Al—Ni catalyst. Heat to reflux for 18 h, cool to 60° C., dilute with MeOH (30 mL), and resume heating. When reflux has begun, filter the reaction mixture while hot through filter paper. Concentrate the filtrate in-vacuo. Dilute the residue with water (30 mL) and saturated aqueous NaHCO3 (30 mL), then extract into EtOAc (3×150 mL). Dry the organics (MgSO4), filter, and concentrate to give 2.25g (89%) of the title compound as a brown solid. MS (ES): m/z 393 (M+1); HPLC (Method B): Rt=4.57 min (91%).

Workup

  1. temperatureHeat
  2. temperatureto reflux for 18 h
  3. temperaturecool to 60° C.
  4. temperatureresume heating
  5. temperatureWhen reflux
  6. filtrationfilter the reaction mixture while hot
  7. filtrationthrough filter paper
  8. concentrationConcentrate the filtrate in-vacuo
  9. additionDilute the residue with water (30 mL) and saturated aqueous NaHCO3 (30 mL)
  10. extractionextract into EtOAc (3×150 mL)
  11. dry with materialDry the organics (MgSO4)
  12. filtrationfilter
  13. concentrationconcentrate

Sources & evidence

ORD record
ord-5d323cdac761418fb024f1de4a4d3e66
Source dataset
uspto-grants-2011_05
Patent number
US07935722B2

Reaction notes

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