HCID 178439899, compound → 7-Methyl-2-propyl-1-[2'-(1H-tetrazol-5-yl)biphenyl-4-ylmethyl]-1H-benzoimidazole-5-carboxylic acid ((R)-1-benzyl-2-hydroxycarbamoylethyl)amide

HRID 1895509Notes

Reaction equation

HRID 1895509 reaction equation
C([C@@H](NC(C1C=C(C)C2N=C(CCC)N(CC3C=CC(C4C=CC=CC=4C4NN=NN=4)=CC=3)C=2C=1)=O)CC(=O)NOCC1C=CC=CC=1)C1C=CC=CC=1.[CH2:55]([C@@H:62]([NH:75][C:76]([C:78]1[CH:107]=[C:106]([CH3:108])[C:81]2[N:82]([CH2:88][C:89]3[CH:94]=[CH:93][C:92]([C:95]4[CH:100]=[CH:99][CH:98]=[CH:97][C:96]=4[C:101]4[NH:105][N:104]=[N:103][N:102]=4)=[CH:91][CH:90]=3)[C:83]([CH2:85][CH2:86][CH3:87])=[N:84][C:80]=2[CH:79]=1)=[O:77])[CH2:63][C:64](=[O:74])[NH:65][O:66]CC1C=CC=CC=1)[C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=1>CCO.C(O)(=O)C.[Pd]>[CH2:55]([C@@H:62]([NH:75][C:76]([C:78]1[CH:107]=[C:106]([CH3:108])[C:81]2[N:82]([CH2:88][C:89]3[CH:94]=[CH:93][C:92]([C:95]4[CH:100]=[CH:99][CH:98]=[CH:97][C:96]=4[C:101]4[NH:102][N:103]=[N:104][N:105]=4)=[CH:91][CH:90]=3)[C:83]([CH2:85][CH2:86][CH3:87])=[N:84][C:80]=2[CH:79]=1)=[O:77])[CH2:63][C:64](=[O:74])[NH:65][OH:66])[C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=1

Participants

6

Reactant 2

HCID 178439899HCID 178439899, compoundHCID 178439951HCID 178439951, compound

Product 1

HCID 1784399527-Methyl-2-propyl-1-[2'-(1H-tetrazol-5-yl)biphenyl-4-ylmethyl]-1H-benzoimidazole-5-carboxylic acid ((R)-1-benzyl-2-hydroxycarbamoylethyl)amide

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

A mixture of 7-methyl-2-propyl-3-[2′-(1H-tetrazol-5-yl)biphenyl-4-ylmethyl]-3H-benzoimidazole-5-carboxylic acid ((R)-1-benzyl-2-benzyloxycarbamoylethyl)amide and 7-methyl-2-propyl-1-[2′-(1H-tetrazol-5-yl)biphenyl-4-ylmethyl]-1H-benzoimidazole-5-carboxylic acid ((R)-1-benzyl-2-benzyloxycarbamoylethyl)amide were dissolved in EtOH (50 mL), followed by the addition of 10% Pd/C (200 mg). The final mixture was bubbled with nitrogen gas for 5 minutes, and degassed. The reaction mixture was stirred under hydrogen (1 atm) for 12 hours, and filtered through Celite®. The filtrate was concentrated to afford a pale brown oil. The oil was dissolved in 50% aqueous acetic acid, and purified by reversed phase preparative HPLC. The desired product, compound 2-b (minor component), was isolated as a colorless solid.

Workup

  1. customThe final mixture was bubbled with nitrogen gas for 5 minutes
  2. customdegassed
  3. filtrationfiltered through Celite®
  4. concentrationThe filtrate was concentrated
  5. customto afford a pale brown oil
  6. custompurified by reversed phase preparative HPLC

Sources & evidence

ORD record
ord-66027e6dfc494a4ba0ea6e2a1a9c56e7
Source dataset
uspto-grants-2013_08
Patent number
US08513432B2

Reaction notes

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