Sodium Hydroxide → HCID 178458676, compound

HRID 518733Notes

Reaction equation

HRID 518733 reaction equation
[F:1][C:2]1[CH:40]=[CH:39][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][CH:32]([C:35]([OH:38])([CH3:37])[CH3:36])[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:40]=[CH:39][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[CH2:30][CH2:31][CH:32]([C:35]([OH:38])([CH3:36])[CH3:37])[CH2:33][CH2:34]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:4][CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178501182HCID 178501182, compound

Product 1

HCID 178458676HCID 178458676, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of cis-methyl 4-((E)-2-(4-fluorobenzoylimino)-6-((4-(2-hydroxypropan-2-yl)piperidin-1-yl)methyl)-2,3-dihydro-1H-benzo[d]imidazol-1-yl)cyclohexanecarboxylate (1.05 g, 1.907 mmol) in MeOH (20 mL) was added 1 N aqueous NaOH (19.07 mL, 19.07 mmol). The solution was stirred overnight at RT. After 2 days, the reaction solution was concentrated, the pH was adjusted to 4 with 2 N aqueous HCl, and the mixture was extracted with 9:1 DCM/2-propanol. The organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated to generate cis-4-((E)-2-(4-fluorobenzoylimino)-6-((4-(2-hydroxypropan-2-yl)piperidin-1-yl)methyl)-2,3-dihydro-1H-benzo[d]imidazol-1-yl)cyclohexanecarboxylic acid (1.01 g, 1.882 mmol, 99% yield) as a white powder. MS, m/z (C30H37PN4O4): calcd, 536.3. found, 537.0 [M+H].

Workup

  1. waitAfter 2 days
  2. concentrationthe reaction solution was concentrated
  3. extractionthe mixture was extracted with 9:1 DCM/2-propanol
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f7d8a2f8dc484a1289bea19a9ee5b1d1
Source dataset
uspto-grants-2015_08
Patent number
US09115127B2

Reaction notes

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