Dichloromethane → HCID 22724200, compound

HRID 2086871Notes

Reaction equation

HRID 2086871 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:28]([CH2:31][CH3:32])[CH2:29][CH3:30])C.[C:33](OCC)(=O)[CH3:34].[C:39](=[O:42])(O)[O-].[Na+].Cl[CH2:45]Cl>>[CH2:15]([C:12]1[C:13](=[O:14])[N:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([NH:1][C:39](=[O:42])/[CH:33]=[CH:34]/[C:32]3[CH:31]=[N:28][CH:29]=[CH:30][CH:45]=3)[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

6

Reactant 5

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 22724309HCID 22724309, compound

Product 1

HCID 22724200HCID 22724200, compound

Procedure

To a mixture of 4-(3-aminophenyl)-2-benzyl-3-oxo-3,4-dihydropyrido[2,3-b]pyrazine (150 mg) and triethylamine (0.16 ml) in dichloromethane (3 ml) was added 3-((E)-3-pyridyl]acryloyl chloride-hydrochloride (140 mg). The mixture was stirred at room temperature for 30 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 residue was crystallized from methanol to give 2-benzyl-4-[3-[(E)-3-(3-pyridyl)acryloylamino]phenyl]-3-oxo-3,4-dihydropyrido[2,3-b]pyrazine (138 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 residue was crystallized from methanol

Sources & evidence

ORD record
ord-7ad14bd079264150a046e96c8571d408
Source dataset
uspto-grants-2004_04
Patent number
US06727245B2

Reaction notes

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