Dimethylformamide → HCID 22724298, compound

HRID 2231017Notes

Reaction equation

HRID 2231017 reaction equation
[C:1]1([CH2:11][C:12]([OH:14])=O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.C(Cl)(=O)C(Cl)=O.CN(C)C=O.[NH2:26][C:27]1[CH:28]=[C:29]([N:33]2[C:38](=[O:39])[C:37]([CH2:40][C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)=[N:36][C:35]3[CH:47]=[CH:48][CH:49]=[N:50][C:34]2=3)[CH:30]=[CH:31][CH:32]=1>ClCCl.O.C(OCC)(=O)C.C(N(CC)CC)C>[CH2:40]([C:37]1[C:38](=[O:39])[N:33]([C:29]2[CH:30]=[CH:31][CH:32]=[C:27]([NH:26][C:12](=[O:14])[CH2:11][C:1]3[C:10]4[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=4)[CH:4]=[CH:3][CH:2]=3)[CH:28]=2)[C:34]2[N:50]=[CH:49][CH:48]=[CH:47][C:35]=2[N:36]=1)[C:41]1[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1

Participants

9

Reactant 4

HCID 6228DimethylformamideHCID 68621-Naphthaleneacetic AcidHCID 65578Oxalyl chlorideHCID 22724309HCID 22724309, compound

Product 1

HCID 22724298HCID 22724298, compoundYield 62.1%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1-naphthylacetic acid (82 mg), oxalyl chloride (0.02 ml) and catalytic amount of N,N-dimethylformamide in dichloromethane (2 ml) was stirred at room temperature for 30 minutes. The above solution was added to a mixture of 4-(3-aminophenyl)-3-oxo-2-benzyl-3,4-dihydropyrido[2,3-b]pyrazine (131 mg) and triethylamine (0.085 ml) in dichloromethane (2 ml). The mixture was stirred at room temperature for 30 minutes, then poured into a mixture of ethyl acetate add water. The organic phase was washed with aqueous sodium bicarbonate solution and brine, dried over magnesium sulfate and concentrated. The residue was crystallized with ethanol to give 2-benzyl-3-oxo-4-[3-[(1-naphthyl)acetylamino]phenyl]-3,4-dihydropyrido[2,3-b]pyrazine (123 mg).

Workup

  1. stirringThe mixture was stirred at room temperature for 30 minutes
  2. washThe organic phase was washed with aqueous sodium bicarbonate solution and brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was crystallized with ethanol

Sources & evidence

ORD record
ord-c2d72370b56143e39edeb99964eb6ae8
Source dataset
uspto-grants-2002_07
Patent number
US06426345B1

Reaction notes

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