HCID 59497653, compound → HCID 59497441, compound

HRID 1747452Notes

Reaction equation

HRID 1747452 reaction equation
[O:1]=[C:2]1[N:6]([CH:7]([CH2:12][CH2:13][CH3:14])[CH2:8][C:9]([OH:11])=[O:10])[C:5]2[CH:15]=[CH:16][CH:17]=[CH:18][C:4]=2[N:3]1[CH2:19][C:20]1[CH:21]=[C:22]([Br:33])[CH:23]=[C:24]2[C:28]=1[N:27]([CH3:29])[C:26](=[O:30])[C:25]2(Br)Br>C(O)(=O)C.[Zn]>[Br:33][C:22]1[CH:23]=[C:24]2[C:28](=[C:20]([CH2:19][N:3]3[C:4]4[CH:18]=[CH:17][CH:16]=[CH:15][C:5]=4[N:6]([CH:7]([CH2:12][CH2:13][CH3:14])[CH2:8][C:9]([OH:11])=[O:10])[C:2]3=[O:1])[CH:21]=1)[N:27]([CH3:29])[C:26](=[O:30])[CH2:25]2

Participants

4

Reactant 1

HCID 59497653HCID 59497653, compound

Product 1

HCID 59497441HCID 59497441, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of 3-[2-Oxo-3-(3,3,5-tribromo-1-methyl-2-oxo-2,3-dihydro-1H-indol-7-ylmethyl)-2,3-dihydro-benzimidazol-1-yl]-hexanoic acid (20 mg, 0.031 mmol) in acetic acid (5 mL) was added Zinc powder (10 mg, 0.16 mmol) at room temperature. The mixture was stirred at the same temperature for 30 minutes. The mixture was filtered and the filtrate was concentrated. The residue was cool in an ice bath and water was added. The solid that precipitate out from the solution was collected by filtration and was washed with water. The white solid was dried in an oven and was confirmed to be the desirable product (8.9 mg, 59%). LCMS (ESMS): m/z 488.12 (M+H+).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. temperatureThe residue was cool in an ice bath
  4. additionwater was added
  5. filtrationThe solid that precipitate out from the solution was collected by filtration
  6. washwas washed with water
  7. customThe white solid was dried in an oven

Sources & evidence

ORD record
ord-61ff25183fd9488bae966609f529463c
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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