HCID 71278536, compound → HCID 178452356, compound

HRID 1749907Notes

Reaction equation

HRID 1749907 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]2[C:6](=[O:9])[CH2:7][O:8][C:4]=2[C:3]=1[C:12]([N:14]1[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]1)=[O:13].[NH:27]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:29]([CH:36]=O)=[N:28]1>CO.N1CCCCC1>[NH:27]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:29](/[CH:36]=[C:7]2\[O:8][C:4]3[C:3]([C:12]([N:14]4[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]4)=[O:13])=[C:2]([OH:1])[CH:11]=[CH:10][C:5]=3[C:6]\2=[O:9])=[N:28]1

Participants

5

Reactant 2

HCID 71278536HCID 71278536, compoundHCID 178520025HCID 178520025, compound

Product 1

HCID 178452356HCID 178452356, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

A solution of tert-butyl 4-(6-hydroxy-3-oxo-2,3-dihydrobenzofuran-7-carbonyl)piperazine-1-carboxylate (0.048 g, 0.13 mmol) in methanol (2.0 mL) was added with 1H-indazole-3-carboxaldehyde (0.025 g, 0.17 mmol). Then, the mixture was added with 7 drops of piperidine, and the mixture was stirred at 50° C. for 4 hours. The solid formed was removed by filtration, the filtrate was concentrated, and then the residue was subjected to silica gel column chromatography (eluted with chloroform/methanol (97:3→90:10)) to obtain tert-butyl (Z)-4-{2-[(1H-indazol-3-yl)methylene]-6-hydroxy-3-oxo-2,3-dihydrobenzofuran-7-carbonyl}piperazine-1-carboxylate (0.054 g, 85%).

Workup

  1. customThe solid formed
  2. customwas removed by filtration
  3. concentrationthe filtrate was concentrated
  4. washthe residue was subjected to silica gel column chromatography (eluted with chloroform/methanol (97:3→90:10))

Sources & evidence

ORD record
ord-4a1f4c155e1043a29036c3f61a2a0cc6
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

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