Sodium Hydroxide → HCID 178522616, compound

HRID 518727Notes

Reaction equation

HRID 518727 reaction equation
[F:1][C:2]1[CH:36]=[CH:35][C:5]([C:6](/[N:8]=[C:9]2\[NH:10][C:11]3[CH:27]=[CH:26][C:25]([CH2:28][N:29]4[CH2:34][CH2:33][O:32][CH2:31][CH2:30]4)=[CH:24][C:12]=3[N:13]\2[C@@H:14]2[CH2:19][CH2:18][C@H:17]([C:20]([O:22]C)=[O:21])[CH2:16][CH2:15]2)=[O:7])=[CH:4][CH:3]=1.[OH-].[Na+]>CO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:6](/[N:8]=[C:9]2\[NH:10][C:11]3[CH:27]=[CH:26][C:25]([CH2:28][N:29]4[CH2:34][CH2:33][O:32][CH2:31][CH2:30]4)=[CH:24][C:12]=3[N:13]\2[C@@H:14]2[CH2:19][CH2:18][C@H:17]([C:20]([OH:22])=[O:21])[CH2:16][CH2:15]2)=[O:7])=[CH:35][CH:36]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178501184HCID 178501184, compound

Product 1

HCID 178522616HCID 178522616, compoundYield 102.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of cis-methyl 4-((E)-2-(4-fluorobenzoylimino)-6-(morpholinomethyl)-2,3-dihydro-1H-benzo[d]imidazol-1-yl)cyclohexanecarboxylate (2.3 g, 4.65 mmol) in MeOH (46.5 mL) was added 1 N aqueous sodium hydroxide (46.5 mL, 46.5 mmol). The suspension wa stirred overnight at RT. The resulting solution was concentrated, adjusted to a pH of approximately 4 with 2 N aqueous HCl, and extracted with DCM. The organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated to generate cis-4-((E)-2-(4-fluorobenzoylimino)-6-(morpholinomethyl)-2,3-dihydro-1H-benzo[d]imidazol-1-yl)cyclohexanecarboxylic acid as a white powder (2.29 g, 102% yield). MS, m/z (C26H29FN4O4): calcd, 480.2. found, 480.2 (M).

Workup

  1. concentrationThe resulting solution was concentrated
  2. extractionextracted with DCM
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-f67efaa083eb440b944c616716f6046d
Source dataset
uspto-grants-2015_08
Patent number
US09115127B2

Reaction notes

Loading…