Water → HCID 68999942, compound

HRID 1821383Notes

Reaction equation

HRID 1821383 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](/[CH:10]=[CH:11]/[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[NH2:18])=[N:2]1.N1C=CC=CC=1.[N:25]1[CH:30]=[CH:29][CH:28]=[C:27]2[C:31]([O:33][C:34](=[O:35])[C:26]=12)=[O:32].O.C1COCC1>>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](/[CH:10]=[CH:11]/[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[NH:18][C:34]([C:26]2[N:25]=[CH:30][CH:29]=[CH:28][C:27]=2[C:31]([OH:33])=[O:32])=[O:35])=[N:2]1.[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](/[CH:10]=[CH:11]/[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[NH:18][C:31]([C:27]2[C:26]([C:34]([OH:35])=[O:33])=[N:25][CH:30]=[CH:29][CH:28]=2)=[O:32])=[N:2]1

Participants

7

Reactant 5

HCID 962WaterHCID 1049PyridineHCID 8028TetrahydrofuranHCID 69688Furo[3,4-b]pyridine-5,7-dioneHCID 69001756HCID 69001756, compound

Product 2

HCID 68999942HCID 68999942, compoundYield 76.2%HCID 69002709HCID 69002709, compound

Procedure

To a solution of Compound 2 (0.10 g, 0.43 mmol) in THF (2.0 mL), pyridine (0.10 μL, 1.3 mmol) and 2,3-pyridinedicarboxylic anhydride (76 mg, 0.51 mmol) were added and stirred at room temperature for 1.5 hours. The reaction mixture was added with water, extracted with ethyl acetate and the organic layer was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform to chloroform/methanol=90/10), crystallized from ethyl acetate to obtain (E)-2-{2-[2-(1H-indazol-3-yl)vinyl]phenylcarbamoyl}nicotinic acid or (E)-3-{2-[2-(1H-indazol-3-yl)vinyl]phenylcarbamoyl}pyridine-2-carboxylic acid (63 mg, 39%).

Workup

  1. extractionextracted with ethyl acetate
  2. concentrationthe organic layer was concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (chloroform to chloroform/methanol=90/10)
  4. customcrystallized from ethyl acetate

Sources & evidence

ORD record
ord-77afc23341cf495c94153496690c1b10
Source dataset
uspto-grants-2009_10
Patent number
US07605272B2

Reaction notes

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