Pyridine → HCID 123392000, compound

HRID 406266Notes

Reaction equation

HRID 406266 reaction equation
[OH:1][CH:2]1[CH2:23][N:22]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C:5]2=[N:6][C:7]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[C:8]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[N:9]=[C:4]2[CH:3]1[OH:31].[C:32](OC(=O)C)(=[O:34])[CH3:33].N1[CH:44]=[CH:43]C=CC=1.C(=O)(O)[O-:46].[Na+]>>[C:32]([O:1][CH:2]1[CH2:23][N:22]([C:24]([O:26][C:27]([CH3:28])([CH3:30])[CH3:29])=[O:25])[C:5]2=[N:6][C:7]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[C:8]([C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:9]=[C:4]2[CH:3]1[O:31][C:43](=[O:46])[CH3:44])(=[O:34])[CH3:33]

Participants

5

Reactant 4

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 66665861rac-tert-butyl 7,8-dihydroxy-2,3-diphenyl-7,8-dihydropyrido[2,3-b]pyrazine-5(6H)-carboxylate

Product 1

HCID 123392000HCID 123392000, compound

Procedure

A mixture comprising the rac-tert-butyl 7,8-dihydroxy-2,3-diphenyl-7,8-dihydropyrido[2,3-b]pyrazine-5(6H)-carboxylate (step 2) (230 mg, 0.548 mmol), acetic anhydride (155 μl, 1.645 mmol) and pyridine (1064 μl, 13.16 mmol) was stirred at RT under an atmosphere of nitrogen overnight. After standing at RT for 2 days, the mixture was diluted with saturated sodium bicarbonate and extracted with DCM (2×20 ml). The organic extracts were combined and concentrated in vacuo. The crude material was purified by chromatography on silica eluting with 20-100% EtOAc/iso-hexane to afford the title compound;

Workup

  1. waitAfter standing at RT for 2 days
  2. extractionextracted with DCM (2×20 ml)
  3. concentrationconcentrated in vacuo
  4. customThe crude material was purified by chromatography on silica eluting with 20-100% EtOAc/iso-hexane

Sources & evidence

ORD record
ord-f6364deff7254547bb24568b7179515d
Source dataset
uspto-grants-2014_06
Patent number
US08754085B2

Reaction notes

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