Sodium Hydroxide → HCID 178522620, compound

HRID 518613Notes

Reaction equation

HRID 518613 reaction equation
[C:1](/[N:9]=[C:10]1/[N:11]([C@@H:28]2[CH2:33][CH2:32][C@H:31]([C:34]([O:36]C)=[O:35])[CH2:30][CH2:29]2)[C:12]2[CH:17]=[C:16]([O:18][CH2:19][CH2:20][N:21]3[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]3)[N:15]=[CH:14][C:13]=2[NH:27]/1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>CO>[C:1](/[N:9]=[C:10]1/[N:11]([C@@H:28]2[CH2:29][CH2:30][C@H:31]([C:34]([OH:36])=[O:35])[CH2:32][CH2:33]2)[C:12]2[CH:17]=[C:16]([O:18][CH2:19][CH2:20][N:21]3[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]3)[N:15]=[CH:14][C:13]=2[NH:27]/1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178501177HCID 178501177, compound

Product 1

HCID 178522620HCID 178522620, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of cis-methyl 4-((E)-2-(benzoylimino)-6-(2-(piperidin-1-yl)ethoxy)-2,3-dihydro-1H-imidazo[4,5-c]pyridin-1-yl)cyclohexanecarboxylate (0.052 g, 0.103 mmol) in MeOH (1.0 mL) was added 1N aqueous NaOH (1.028 mL, 1.028 mmol), and the resulting mixture was stirred at RT for 48 hours. The reaction mixture was concentrated under vacuum to remove MeOH and neutralized with 2 N HCl. The product was extracted with DCM (5-20 mL) to afford cis-4-((E)-2-(benzoylimino)-6-(2-(piperidin-1-yl)ethoxy)-2,3-dihydro-1H-imidazo[4,5-c]pyridin-1-yl)cyclohexanecarboxylic acid as an off-white solid (50 mg, 99% yield). MS m/z=492.2 [M+H]. Calc'd for C27H33N5O4: 491.3.

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. customto remove MeOH
  3. extractionThe product was extracted with DCM (5-20 mL)

Sources & evidence

ORD record
ord-5636ef10ee964f268ba955f2ea32931c
Source dataset
uspto-grants-2015_08
Patent number
US09115127B2

Reaction notes

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