HCID 136141615, compound → HCID 136141700, compound

HRID 1064199Notes

Reaction equation

HRID 1064199 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[NH:15][C:16]3[CH:17]=[C:18]([NH2:28])[CH:19]=[C:20]4[C:26](=[O:27])[NH:25][N:24]=[CH:23][C:22]=2[C:21]=34)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>[Pd].CO>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([C:14]2[NH:15][C:16]3[CH:17]=[C:18]([NH2:28])[CH:19]=[C:20]4[C:26](=[O:27])[NH:25][N:24]=[CH:23][C:22]=2[C:21]=34)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 136141615HCID 136141615, compound

Product 1

HCID 136141700HCID 136141700, compoundYield 29.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

In a manner analogous to that of Example 183, palladium (10% on activated carbon) (0.186 g) was added to a solution of Intermediate 220(a) of Example 220 (0.61 g, 1.60 mmol) in 9:1 methanol:N,N-dimethformamide (50 mL). The reaction mixture was purged with H2 and stirred at room temperature under H2 (1 atm.) for 6.5 hours. The mixture was filtered, and the filtrate evaporated. The resulting residue was dissolved in methanol and loaded onto a silica gel plug. The plug was then loaded onto a silica gel column and eluted with 50:3 dichloromethane:methanol to give Intermediate 222(a) (0.18 g, 0.470 mmol) as a yellow solid in 29% yield.

Workup

  1. customThe reaction mixture was purged with H2
  2. filtrationThe mixture was filtered
  3. customthe filtrate evaporated
  4. dissolutionThe resulting residue was dissolved in methanol
  5. washeluted with 50:3 dichloromethane

Sources & evidence

ORD record
ord-b3fd72141ed54020a152e4ffcf96df02
Source dataset
uspto-grants-2005_11
Patent number
US06967198B2

Reaction notes

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