HCID 71114463, compound → HCID 71089560, compound

HRID 710104Notes

Reaction equation

HRID 710104 reaction equation
F[CH:2](F)[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:10][C:11]3[CH:17]=[C:16]([C:18]4[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH:19]=4)[CH:15]=[CH:14][C:12]=3[N:13]=2)=[CH:5][CH:4]=1>CO.[Pd]>[C:3]1([CH3:2])[CH:4]=[CH:5][C:6]([C:9]2[O:10][C:11]3[CH:17]=[C:16]([CH:18]4[CH2:19][CH2:20][N:21]([C:24]([O:26][C:27]([CH3:29])([CH3:28])[CH3:30])=[O:25])[CH2:22][CH2:23]4)[CH:15]=[CH:14][C:12]=3[N:13]=2)=[CH:7][CH:8]=1

Participants

4

Reactant 1

HCID 71114463HCID 71114463, compound

Product 1

HCID 71089560HCID 71089560, compoundYield 72.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Intermediate 48 (45 mg, 0.14 mmol) dissolved in MeOH (10 ml) and added Pd/C (5%) (100 mg). This mixture was stirred under 60 Psi hydrogen pressure for 15 h in an autoclave. After completion of the reaction, reaction mixture filtered through a bed of celite and celite was washed with MeOH. Combined MeOH layers were removed on rotavapour to obtain the residue. Residue was triturated with petether to obtain the titled compound (40 mg) as an off-white solid. MS (m/z): 393.2 [M+H]+.

Workup

  1. customAfter completion of the reaction, reaction mixture
  2. filtrationfiltered through a bed of celite and celite
  3. washwas washed with MeOH
  4. customCombined MeOH layers were removed on rotavapour
  5. customto obtain the residue
  6. customResidue was triturated with petether

Sources & evidence

ORD record
ord-70298f963f0e4d7aafaaaa015441048b
Source dataset
uspto-grants-2015_11
Patent number
US09181214B2

Reaction notes

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