Triethylamine → HCID 22724081, compound

HRID 2086865Notes

Reaction equation

HRID 2086865 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([N:14]3[C:19](=[O:20])[C:18]([CH2:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[N:17][C:16]4[CH:28]=[CH:29][CH:30]=[N:31][C:15]3=4)[CH:11]=[CH:12][CH:13]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:39][S:40](Cl)(=[O:42])=[O:41].C(=O)(O)[O-].[Na+]>ClCCl.C(OCC)(=O)C>[CH2:21]([C:18]1[C:19](=[O:20])[N:14]([C:10]2[CH:11]=[CH:12][CH:13]=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([NH:1][S:40]([CH3:39])(=[O:42])=[O:41])=[CH:3][CH:4]=3)[CH:9]=2)[C:15]2[N:31]=[CH:30][CH:29]=[CH:28][C:16]=2[N:17]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 22724459HCID 22724459, compound

Product 1

HCID 22724081HCID 22724081, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 4-[3-(4-aminophenyl)phenyl]-2-benzyl-3-oxo-3,4-dihydropyrido[2,3-b]pyrazine (94 mg) and triethylamine (0.04 ml) in dichloromethane (3 ml) was added methanesulfonyl chloride (0.04 ml). 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 chromatographed on silica gel column (35% ethyl acetate in hexane) and crystallized from ethanol to give 2-benzyl-4-[3-(4-methylsulfonylaminophenyl)phenyl]-3-oxo-3,4-dihydropyrido[2,3-b]pyrazine (53 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 chromatographed on silica gel column (35% ethyl acetate in hexane)
  6. customcrystallized from ethanol

Sources & evidence

ORD record
ord-bfa8b1d6decd4260a470a39c95a29ebe
Source dataset
uspto-grants-2004_04
Patent number
US06727245B2

Reaction notes

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