Sodium Hydroxide → 7-(6-oxo-2,3-dip-tolyl-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)heptanoic acid

HRID 406224Notes

Reaction equation

HRID 406224 reaction equation
[O:1]=[C:2]1[N:25]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32]([O:34]CC)=[O:33])[C:6]2=[N:7][C:8]([C:18]3[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=3)=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=3)[N:10]=[C:5]2[CH2:4][CH2:3]1.[OH-].[Na+]>CO>[O:1]=[C:2]1[N:25]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32]([OH:34])=[O:33])[C:6]2=[N:7][C:8]([C:18]3[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=3)=[C:9]([C:11]3[CH:12]=[CH:13][C:14]([CH3:17])=[CH:15][CH:16]=3)[N:10]=[C:5]2[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66665730Ethyl 7-(6-oxo-2,3-dip-tolyl-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)heptanoate

Product 1

HCID 666657007-(6-oxo-2,3-dip-tolyl-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)heptanoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of ethyl 7-(6-oxo-2,3-dip-tolyl-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)heptanoate (550 mg, 1.133 mmol) in methanol (10 ml) was treated with 1M sodium hydroxide (3.40 ml, 3.40 mmol) and the resultant solution was stirred at 50° C. for 1 hour. The solution was cooled to room temperature and concentrated under vacuum. The residue was diluted with water, acidified to pH ˜2 with 1N HCl, giving a white solid which was extracted with DCM (×3). The extracts were dried (MgSO4) and evaporated under vacuum to afford the title compound as a white solid;

Workup

  1. concentrationconcentrated under vacuum
  2. additionThe residue was diluted with water
  3. customgiving a white solid which
  4. extractionwas extracted with DCM (×3)
  5. dry with materialThe extracts were dried (MgSO4)
  6. customevaporated under vacuum

Sources & evidence

ORD record
ord-6bdcb26710bb4c6fac44a0dcf106cfe3
Source dataset
uspto-grants-2014_06
Patent number
US08754085B2

Reaction notes

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