Water → Ethyl 4-(2-(2,3-dip-tolyl-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)ethylamino)-4-oxobutanoate

HRID 406220Notes

Reaction equation

HRID 406220 reaction equation
[C:1]1([CH3:27])[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][NH2:26])[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.C(N([CH2:33][CH3:34])CC)C.C([CH:37]([CH2:41][C:42](Cl)=[O:43])[C:38](Cl)=[O:39])C.[OH2:45]>C(OCC)(=O)C>[C:1]1([CH3:27])[CH:2]=[CH:3][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:42](=[O:43])[CH2:41][CH2:37][C:38]([O:39][CH2:33][CH3:34])=[O:45])[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:5][CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 218646082-Ethylbutanedioyl dichlorideHCID 666659362-(2,3-Dip-tolyl-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)ethanamine

Product 1

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

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture comprising 2-(2,3-dip-tolyl-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)ethanamine (step 2) (108 mg, 0.301 mmol) in ethyl acetate (5 ml) and triethylamine (0.084 ml, 0.603 mmol) at RT was treated dropwise with ethyl succinyl chloride (74.4 mg, 0.452 mmol) and the resulting suspension was stirred at RT for 30 minutes. The mixture was poured into water and extracted with ethyl acetate. The organic layer was separated, dried over and concentrated in vacuo to afford the title compound;

Workup

  1. extractionextracted with ethyl acetate
  2. customThe organic layer was separated
  3. customdried over and
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4182bbc5ebd74ede9648726c6fd7a795
Source dataset
uspto-grants-2014_06
Patent number
US08754085B2

Reaction notes

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