Citric Acid → 7-(7-(Piperidin-1-yl)-2,3-di-p-tolyl-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)heptanoic acid

HRID 517909Notes

Reaction equation

HRID 517909 reaction equation
[N:1]1([CH:7]2[CH2:30][N:29]([CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][C:37]([O:39]CC)=[O:38])[C:10]3=[N:11][C:12]([C:22]4[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=4)=[C:13]([C:15]4[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=4)[N:14]=[C:9]3[CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+].O.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CCO>[N:1]1([CH:7]2[CH2:30][N:29]([CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][C:37]([OH:39])=[O:38])[C:10]3=[N:11][C:12]([C:22]4[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=4)=[C:13]([C:15]4[CH:16]=[CH:17][C:18]([CH3:21])=[CH:19][CH:20]=4)[N:14]=[C:9]3[CH2:8]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 4

HCID 311Citric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 89690354Ethyl 7-(7-(piperidin-1-yl)-2,3-di-p-tolyl-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)heptanoate

Product 1

HCID 896940827-(7-(Piperidin-1-yl)-2,3-di-p-tolyl-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)heptanoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of ethyl 7-(7-(piperidin-1-yl)-2,3-di-p-tolyl-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)heptanoate (step 8) (39 mg, 0.070 mmol) in EtOH (1 ml) was treated with 2M NaOH (0.105 mL, 0.211 mmol) and stirred at room temperature overnight. The resulting mixture was added to water (30 ml) and the pH was adjusted to pH4 by addition of 10% aqueous citric acid solution. The aqueous portion was extracted with DCM (×3) and the combined extracts were passed through a phase separating column. The solvent was removed under reduced pressure to afford the titled compound;

Workup

  1. extractionThe aqueous portion was extracted with DCM (×3)
  2. customseparating column
  3. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-818c966ed5a24b1082cc9e79cd1901ac
Source dataset
uspto-grants-2015_08
Patent number
US09115129B2

Reaction notes

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