Ammonia → HCID 22724032, compound

HRID 2231058Notes

Reaction equation

HRID 2231058 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:21](O)=[O:22])[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.C(Cl)(=O)C(Cl)=O.[NH3:34].C(=O)(O)[O-].[Na+]>ClCCl.CN(C)C=O.C(OCC)(=O)C>[CH2:1]([C:8]1[C:13](=[O:14])[N:12]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21](=[O:22])[NH2:34])[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

8

Reactant 4

HCID 222AmmoniaHCID 65578Oxalyl chlorideHCID 516892Sodium BicarbonateHCID 22724010HCID 22724010, compound

Product 1

HCID 22724032HCID 22724032, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-benzyl-4-(3-carboxyphenyl)-3-oxo-3,4-dihydropyrido[2,3-b]pyrazine (41 mg) in dichloromethane (2 ml) was added oxalyl chloride (0.02 ml) and 1 drop of N,N-dimethylformamide. After stirring at room temperature for 15 minutes, ammonia solution (28%, 1 ml) was added to the mixture and stirred at room temperature for 15 minutes. The mixture was 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 isopropyl ether to give 2-benzyl-4-(3-carbamoylphenyl)-3-oxo-3,4-dihydropyrido[2,3-b]pyrazine (139 mg).

Workup

  1. stirringstirred at room temperature for 15 minutes
  2. customThe organic phase was separated
  3. washwashed with aqueous sodium bicarbonate and brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe resultant solid was collected
  7. washwashed with isopropyl ether

Sources & evidence

ORD record
ord-c4f1f1cb4357456380bd2fabc062adb1
Source dataset
uspto-grants-2002_07
Patent number
US06426345B1

Reaction notes

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