Sodium Hydroxide → 4-(2-(2,3-Dip-tolyl-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)ethylamino)-4-oxobutanoic acid

HRID 406221Notes

Reaction equation

HRID 406221 reaction equation
[C:1]1([CH3:36])[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][NH:26][C:27](=[O:35])[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.[OH-].[Na+]>CCO>[C:1]1([CH3:36])[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][NH:26][C:27](=[O:35])[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

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66666378Ethyl 4-(2-(2,3-dip-tolyl-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)ethylamino)-4-oxobutanoate

Product 1

HCID 666660714-(2-(2,3-Dip-tolyl-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)ethylamino)-4-oxobutanoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 4-(2-(2,3-dip-tolyl-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)ethylamino)-4-oxobutanoate (step 3)(168 mg, 0.345 mmol) was dissolved in EtOH (3 ml). 2M Sodium hydroxide (0.345 ml, 0.690 mmol) was added and the solution stirred for 30 minutes at room temperature. The reaction mixture was concentrated in vacuo and the residue was partitioned between EtOAc and 0.1 M HCl solution. The organic layer was separated and washed with saturated brine, dried (MgSO4) and concentrated in vacuo to a volume of 5 ml. The suspension was filtered and washed with EtOAc to afford the title compound;

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue was partitioned between EtOAc and 0.1 M HCl solution
  3. customThe organic layer was separated
  4. washwashed with saturated brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo to a volume of 5 ml
  7. filtrationThe suspension was filtered
  8. washwashed with EtOAc

Sources & evidence

ORD record
ord-caef1a7c81884d38839335fbd400e7e2
Source dataset
uspto-grants-2014_06
Patent number
US08754085B2

Reaction notes

Loading…