HCID 59497483, compound → HCID 25128174, compound

HRID 1747479Notes

Reaction equation

HRID 1747479 reaction equation
C([O:3][C:4](=[O:31])[CH2:5][CH:6]([N:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[N:12]([CH2:19][C:20]2[CH:28]=[C:27]([Cl:29])[CH:26]=[C:25]3[C:21]=2[CH:22]=[CH:23][NH:24]3)[C:11]1=[O:30])[CH2:7][CH2:8][CH3:9])C>CO>[Cl:29][C:27]1[CH:26]=[C:25]2[C:21]([CH:22]=[CH:23][NH:24]2)=[C:20]([CH2:19][N:12]2[C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[N:10]([CH:6]([CH2:7][CH2:8][CH3:9])[CH2:5][C:4]([OH:31])=[O:3])[C:11]2=[O:30])[CH:28]=1

Participants

3

Reactant 1

HCID 59497483HCID 59497483, compound

Product 1

HCID 25128174HCID 25128174, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-[3-(6-Chloro-1H-indol-4-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-hexanoic acid ethyl ester (100 mg, 0.23 mmol), prepared as described in example 72 using the appropriate reagents, was dissolved in methanol (1 mL) and treated with Amberlyst® A26 (OH— form) (1.2 g, 1.6 mmol). The resulting mixture was agitated 18 h. The mixture was filtered and the resin was washed with several portions of methanol. The product was eluted from the resin with 20% formic acid in methanol (2×2 mL). The solution was concentrated and purified by preparative HPLC using an acetonitrile/water/formic acid gradient to provide 50 mg (53%) of the title compound. LCMS (ESMS): m/z 412 (M+H).

Workup

  1. additiontreated with Amberlyst® A26 (OH— form) (1.2 g, 1.6 mmol)
  2. filtrationThe mixture was filtered
  3. washthe resin was washed with several portions of methanol
  4. washThe product was eluted from the resin with 20% formic acid in methanol (2×2 mL)
  5. concentrationThe solution was concentrated
  6. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-8ae56873c7f041f1ab58fbfc4f36048f
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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