Acetic Anhydride → HCID 22724145, compound

HRID 2086875Notes

Reaction equation

HRID 2086875 reaction equation
[C:1]1([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:6]=[CH:5][CH:4]=[C:3]([N:7]2[C:12](=[O:13])[C:11]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=3)=[N:10][C:9]3[CH:22]=[CH:23][CH:24]=[N:25][C:8]2=3)[CH:2]=1.C(N(CC)CC)C.[C:39](OC(=O)C)(=[O:41])[CH3:40].C(=O)(O)[O-].[Na+]>CN(C)C1C=CN=CC=1.O1CCOCC1.C(OCC)(=O)C>[C:39]([O:21][C:18]1[CH:17]=[CH:16][C:15]([CH2:14][C:11]2[C:12](=[O:13])[N:7]([C:3]3[CH:2]=[C:1]([C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=4)[CH:6]=[CH:5][CH:4]=3)[C:8]3[N:25]=[CH:24][CH:23]=[CH:22][C:9]=3[N:10]=2)=[CH:20][CH:19]=1)(=[O:41])[CH3:40]

Participants

8

Reactant 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 22724147HCID 22724147, compound

Product 1

HCID 22724145HCID 22724145, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

To a mixture of 4-(3-biphenylyl)-2-(4-hydroxybenzyl)-3-oxo-3,4-dihydropyrido[2,3-b]pyrazine (76 mg), triethylamine (0.05 ml) and 4-dimethylaminopyridine (3 mg) in 1,4-dioxane (2 ml) was added acetic anhydride (0.035 ml). The mixture was stirred at room temperature for 1 hour, 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 to give 2-(4-acetoxybenzyl)-4-(3-biphenylyl)-3-oxo-3,4-dihydropyrido[2,3-b]pyrazine (58 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

Sources & evidence

ORD record
ord-5342436ce28540e7a53db9ff0e14e6e0
Source dataset
uspto-grants-2004_04
Patent number
US06727245B2

Reaction notes

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