Ammonium formate → HCID 59497470, compound

HRID 1747482Notes

Reaction equation

HRID 1747482 reaction equation
Br[C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][N:8]2[CH3:11])=[C:4]([CH2:12][N:13]2[C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=3[N:15]([CH:22]([CH2:27][CH2:28][CH3:29])[CH2:23][C:24]([OH:26])=[O:25])[C:14]2=[O:30])[CH:3]=1.C([O-])=[O:32].[NH4+]>CO>[CH3:11][N:8]1[C:9]2[C:5](=[C:4]([CH2:12][N:13]3[C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=4[N:15]([CH:22]([CH2:27][CH2:28][CH3:29])[CH2:23][C:24]([OH:26])=[O:25])[C:14]3=[O:30])[CH:3]=[CH:2][CH:10]=2)[CH2:6][C:7]1=[O:32]

Participants

4

Reactant 2

HCID 2723923Ammonium formateHCID 59497272HCID 59497272, compound

Product 1

HCID 59497470HCID 59497470, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-[3-(6-bromo-1-methyl-1H-indol-4-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-hexanoic acid (25 mg, 0.05 mmol) in methanol (2 mL) was added ammonium formate (150 mg, 2.4 mmol) and PdC 10% (5 mg). The resulting mixture was agitated for 60 h, filtered and concentrated. The resulting residue was dispersed in DCM (2 mL), filtered, and the filtrate was washed with DCM (1×2 mL). The mother liquors were concentrated and the residue was purified by preparative HPLC using an acetonitrile/water/formic acid gradient to provide 7 mg (35%) of the title compound. LCMS (ESMS): m/z 408 (M+H).

Workup

  1. filtrationfiltered
  2. concentrationconcentrated
  3. additionThe resulting residue was dispersed in DCM (2 mL)
  4. filtrationfiltered
  5. washthe filtrate was washed with DCM (1×2 mL)
  6. concentrationThe mother liquors were concentrated
  7. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-779b87961f0041b38619ba8fb0c43c44
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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