Hydrochloric Acid → HCID 59497374, compound

HRID 1747368Notes

Reaction equation

HRID 1747368 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:13]([CH2:14][N:15]2[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=3[N:17](C(C)=C)[C:16]2=[O:27])=[C:12]2[C:8]([C:9]([CH3:30])=[C:10]([CH3:29])[N:11]2[CH3:28])=[CH:7][CH:6]=1)=[O:4].Cl>CO>[CH3:1][O:2][C:3]([C:5]1[C:13]([CH2:14][N:15]2[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=3[NH:17][C:16]2=[O:27])=[C:12]2[C:8]([C:9]([CH3:30])=[C:10]([CH3:29])[N:11]2[CH3:28])=[CH:7][CH:6]=1)=[O:4]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59497544HCID 59497544, compound

Product 1

HCID 59497374HCID 59497374, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

7-(3-Isopropenyl-2-oxo-2,3-dihydro-benzoimidazol-1-ylmethyl)-1,2,3-trimethyl-1H-indole-6-carboxylic acid methyl ester (100 mg. 0.25 mmol) was dissolved in MeOH (10 mL) and HCl (5 mL) solution at room temperature. The solution was heated to 60 C for 2 hours. The solution was cooled down and was extracted with EtOAc. The combined organic layer was dried with MgSO4 and was filtered. The filtrate was concentrated and the residue was purified by CombiFlash with 10% EtOAc in hexane as the eluent to afford the desirable product 1,2,3-Trimethyl-7-(2-oxo-2,3-dihydro-benzoimidazol-1-ylmethyl)-1H-indole-6-carboxylic acid methyl ester (85 mg, 94%) as a colorless oil.

Workup

  1. customat room temperature
  2. temperatureThe solution was heated to 60 C for 2 hours
  3. temperatureThe solution was cooled down
  4. extractionwas extracted with EtOAc
  5. dry with materialThe combined organic layer was dried with MgSO4
  6. filtrationwas filtered
  7. concentrationThe filtrate was concentrated
  8. customthe residue was purified by CombiFlash with 10% EtOAc in hexane as the eluent

Sources & evidence

ORD record
ord-6a21049a5b5a476f9865543be9d67eae
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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