Hydrochloric Acid → HCID 66965620, compound

HRID 1515017Notes

Reaction equation

HRID 1515017 reaction equation
C[O:2][C:3](=[O:36])[CH2:4][CH2:5][C:6]1[CH:11]=[C:10]([CH3:12])[C:9]([C:13]2[NH:17][C:16]3[CH:18]=[C:19]([C:22](=[O:34])[NH:23][C:24]4[C:33]5[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=5)[CH:27]=[CH:26][N:25]=4)[CH:20]=[CH:21][C:15]=3[N:14]=2)=[C:8]([CH3:35])[CH:7]=1.[OH-].[Na+].Cl>CO>[C:24]1([NH:23][C:22]([C:19]2[CH:20]=[CH:21][C:15]3[N:14]=[C:13]([C:9]4[C:8]([CH3:35])=[CH:7][C:6]([CH2:5][CH2:4][C:3]([OH:36])=[O:2])=[CH:11][C:10]=4[CH3:12])[NH:17][C:16]=3[CH:18]=2)=[O:34])[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:27]=[CH:26][N:25]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66965767HCID 66965767, compound

Product 1

HCID 66965620HCID 66965620, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-{4-[6-(isoquinolin-1-ylcarbamoyl)-1H-benzoimidazol-2-yl]-3,5-dimethylphenyl}-propionic acid methyl ester (85 mg) in MeOH (2 mL) was added 0.5 mL of 1.0 N NaOH and the mixture was stirred at ambient temperature for 18 h. To this solution was added 0.5 mL of 1.0 N HCl then the solvent was removed under reduced pressure. Water was added and the mixture was extracted with EtOAc. The organic phase was dried over sodium sulfate and the solvent was removed under reduced pressure. The residue was triturated with MeCN to give 3-{4-[6-(isoquinolin-1-ylcarbamoyl)-1H-benzoimidazol-2-yl]-3,5-dimethylphenyl}-propionic acid as a tan solid. MS (ESI) m/z 465.1 (M+H), retention time=1.01 min, Method 10.

Workup

  1. customthe solvent was removed under reduced pressure
  2. additionWater was added
  3. extractionthe mixture was extracted with EtOAc
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. customthe solvent was removed under reduced pressure
  6. customThe residue was triturated with MeCN

Sources & evidence

ORD record
ord-203601d4870946a1a248de49b9f2d0a3
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

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