Sodium Hydroxide → HCID 46241111, compound

HRID 410366Notes

Reaction equation

HRID 410366 reaction equation
C[O:2][C:3](=[O:32])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][N:11]2[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=3[N:13]([CH2:20][CH2:21][CH2:22][O:23][C:24]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=3)[C:12]2=[NH:31])[CH:5]=1.[OH-].[Na+]>CO>[F:30][C:27]1[CH:26]=[CH:25][C:24]([O:23][CH2:22][CH2:21][CH2:20][N:13]2[C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[N:11]([CH2:10][C:6]3[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=3)[C:3]([OH:32])=[O:2])[C:12]2=[NH:31])=[CH:29][CH:28]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 46213928HCID 46213928, compound

Product 1

HCID 46241111HCID 46241111, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-{3-[3-(4-fluoro-phenoxy)-propyl]-2-imino-2,3-dihydro-benzoimidazol-1-ylmethyl}-benzoic acid methyl ester (50 mg, 0.12 mmol) in MeOH (2 ml) at rt was added aqueous NaOH (1 ml). The reaction was stirred for 1 h at rt and then it was concentrated under reduced pressure. The material that remained was partitioned between EtOAc and H2O and the 1M KHSO4 was added. The suspension was then filtered and the collected solid was dried to provide 3-{3-[3-(4-fluoro-phenoxy)-propyl]-2-imino-2,3-dihydro-benzoimidazol-1-ylmethyl}-benzoic acid (20 mg, 41%). HPLC-MS 420 [M+1]+.

Workup

  1. concentrationit was concentrated under reduced pressure
  2. customThe material that remained was partitioned between EtOAc and H2O
  3. additionthe 1M KHSO4 was added
  4. filtrationThe suspension was then filtered
  5. customthe collected solid was dried

Sources & evidence

ORD record
ord-6c5a1b02a78f43febed128bba489b794
Source dataset
uspto-grants-2014_06
Patent number
US08759520B2

Reaction notes

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