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

HRID 2276564Notes

Reaction equation

HRID 2276564 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-4772bd028703455eb9ebb6996a8f4115
Source dataset
uspto-grants-2015_09
Patent number
US09132127B2

Reaction notes

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