Lithium Hydroxide → 7-(2-(Pyridin-4-yl)-3-p-tolyl-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)heptanoic acid

HRID 2276573Notes

Reaction equation

HRID 2276573 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[N:8]=[C:9]3[CH2:23][CH2:22][CH2:21][N:20]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30]([O:32]CC)=[O:31])[C:10]3=[N:11][C:12]=2[C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)=[CH:3][CH:2]=1.[Li+].[OH-]>C1COCC1.O>[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[N:8]=[C:9]3[CH2:23][CH2:22][CH2:21][N:20]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30]([OH:32])=[O:31])[C:10]3=[N:11][C:12]=2[C:13]2[CH:14]=[CH:15][C:16]([CH3:19])=[CH:17][CH:18]=2)=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 66666060Ethyl 7-(2-(pyridin-4-yl)-3-p-tolyl-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)heptanoate

Product 1

HCID 666658587-(2-(Pyridin-4-yl)-3-p-tolyl-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)heptanoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of ethyl 7-(2-(pyridin-4-yl)-3-p-tolyl-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)heptanoate (step 4)(65 mg, 0.142 mmol) in THF (3 ml) and water (1 ml) was treated with LiOH (33.9 mg, 1.417 mmol) and the mixture was stirred at room temperature for 16 hours. The mixture was concentrated under vacuum and the residue was diluted with water and washed with EtOAc (×2). The aqueous was acidified (1 N HCl, pH ˜5) and extracted with EtOAc. The combined extracts were washed with brine, dried (MgSO4) and evaporated under vacuum to a yellow gum which was triturated with ether to afford the title compound;

Workup

  1. concentrationThe mixture was concentrated under vacuum
  2. additionthe residue was diluted with water
  3. washwashed with EtOAc (×2)
  4. extractionextracted with EtOAc
  5. washThe combined extracts were washed with brine
  6. dry with materialdried (MgSO4)
  7. customevaporated under vacuum to a yellow gum which
  8. customwas triturated with ether

Sources & evidence

ORD record
ord-18fe222d76db40c79797edc4963ef6a1
Source dataset
uspto-grants-2015_09
Patent number
US09132127B2

Reaction notes

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