HCID 118046608, compound → HCID 118046030, compound

HRID 596120Notes

Reaction equation

HRID 596120 reaction equation
[C:1]([O:5][C:6]([N:8]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[C:9]1[C:10]([C:22]2[CH:34]=[CH:33][C:25]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])=[C:24]([F:35])[CH:23]=2)=[N:11][C:12]([C:15]2[CH2:20][CH2:19][CH2:18][C:17](=[O:21])[CH:16]=2)=[CH:13][N:14]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.C(Cl)Cl.[Pd]>[C:1]([O:5][C:6]([N:8]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[C:9]1[C:10]([C:22]2[CH:34]=[CH:33][C:25]([C:26]([O:28][C:29]([CH3:31])([CH3:32])[CH3:30])=[O:27])=[C:24]([F:35])[CH:23]=2)=[N:11][C:12]([CH:15]2[CH2:20][CH2:19][CH2:18][C:17](=[O:21])[CH2:16]2)=[CH:13][N:14]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 1

HCID 118046608HCID 118046608, compound

Product 1

HCID 118046030HCID 118046030, compoundYield 49.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-(3-(bis(tert-butoxycarbonyl)amino)-6-(3-oxocyclohex-1-en-1-yl)pyrazin-2-yl)-2-fluorobenzoate (3 g, 5.14 mmol) in MeOH (15 mL) and DCM (10 mL) at RT was added Pd—C (10%, degauss, 1.094 g, 1.028 mmol). The resultant mixture was flushed with hydrogen for 10 min, then stirred at RT for 5 hours under hydrogen atmosphere. The suspension was filtered and the solution was concentrated. ISCO silica column separation (80 g silica, 30 min, 5 to 60% EtOAc in Heptane) afforded the desired product as a light yellow sticky liquid, which solidified upon standing over night. (1.485 g, 2.54 mmol, 49.3% yield). LC-MS (m/z): (MH+) 586.3, 1.17 min.

Workup

  1. customThe resultant mixture was flushed with hydrogen for 10 min
  2. filtrationThe suspension was filtered
  3. concentrationthe solution was concentrated
  4. customISCO silica column separation (80 g silica, 30 min, 5 to 60% EtOAc in Heptane)

Sources & evidence

ORD record
ord-720e761f3d89430dacd8a86fdb2d9270
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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