Triethylamine → HCID 22724417, compound

HRID 2086837Notes

Reaction equation

HRID 2086837 reaction equation
[CH2:1]([C:8]1[C:13](=[O:14])[N:12]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17](C(O)=O)[CH:16]=2)[C:11]2[N:24]=[CH:25][CH:26]=[CH:27][C:10]=2[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P([N:42]=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.C(N(CC)CC)C.[C:52]([O:55][CH2:56][CH3:57])(=[O:54])C>C(O)C>[CH2:1]([C:8]1[C:13](=[O:14])[N:12]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([NH:42][C:52]([O:55][CH2:56][CH3:57])=[O:54])[CH:16]=2)[C:11]2[N:24]=[CH:25][CH:26]=[CH:27][C:10]=2[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 199401P,P-Diphenylphosphinic azideHCID 22724010HCID 22724010, compound

Product 1

HCID 22724417HCID 22724417, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-benzyl-4-(3-carboxyphenyl)-3-oxo-3,4-dihydropyrido[2,3-b]pyrazine (166 mg), diphenylphosphoryl azide (128 mg) and triethylamine (47 mg) in ethanol (3 ml) was refluxed for 4 hours. The mixture was poured into ethyl acetate and washed with water and brine, dried over magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography (hexane-ethyl acetate, 1:1) to afford 2-benzyl-4-(3-ethoxycarbonylaminophenyl)-3-oxo-3,4-dihydropyrido[2,3-b]pyrazine (35 mg) as powder.

Workup

  1. temperaturewas refluxed for 4 hours
  2. washwashed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-020acc23f23349bdbf4a59318222f3e1
Source dataset
uspto-grants-2004_04
Patent number
US06727245B2

Reaction notes

Loading…