Triethylamine → HCID 22724098, compound

HRID 2231048Notes

Reaction equation

HRID 2231048 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([N:8]2[C:13](=[O:14])[C:12]([CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[N:11][C:10]3[CH:22]=[CH:23][CH:24]=[N:25][C:9]2=3)[CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.CO[C:35](=[O:39])[C:36](Cl)=[O:37].[C:40](=O)(O)[O-:41].[Na+]>ClCCl.C(OCC)(=O)C>[CH2:15]([C:12]1[C:13](=[O:14])[N:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([N:1]([O:41][CH3:40])[C:35](=[O:39])[CH:36]=[O:37])[CH:3]=2)[C:9]2[N:25]=[CH:24][CH:23]=[CH:22][C:10]=2[N:11]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 79846Methyl chloroglyoxylateHCID 516892Sodium BicarbonateHCID 22724309HCID 22724309, compound

Product 1

HCID 22724098HCID 22724098, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 4-(3-aminophenyl)-2-benzyl-3-oxo-3,4-dihydropyrido[2,3-b]pyrazine (150 mg) and triethylamine (0.1 ml) in dichloromethane (4 ml) was added methoxyglyoxyloyl chloride (0.05 ml). The mixture was stirred at room temperature for 20 minutes, then poured into a mixture of ethyl acetate and aqueous sodium bicarbonate. The organic phase was separated, washed with aqueous sodium bicarbonate and brine, dried over magnesium sulfate and concentrated. The resultant solid was collected and washed with methanol to give 2-benzyl-4-[3-(methoxyglyoxyloylamino)phenyl]-3-oxo-3,4-dihydropyrido[2,3-b]pyrazine (163 mg).

Workup

  1. customThe organic phase was separated
  2. washwashed with aqueous sodium bicarbonate and brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe resultant solid was collected
  6. washwashed with methanol

Sources & evidence

ORD record
ord-8ec2de9e7ad744638f0b41a1dadcfc45
Source dataset
uspto-grants-2002_07
Patent number
US06426345B1

Reaction notes

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