HCID 71278867, compound → HCID 178487199, compound

HRID 1749887Notes

Reaction equation

HRID 1749887 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:6]2[C:7](=[O:10])[CH2:8][O:9][C:5]=2[C:4]=1[CH:13]([N:15]1[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]1)[CH3:14].[NH:28]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[C:30]([CH:37]=O)=[N:29]1>CO.N1CCCCC1>[NH:28]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[C:30](/[CH:37]=[C:8]2\[O:9][C:5]3[C:4]([CH:13]([N:15]4[CH2:16][CH2:17][N:18]([C:21]([O:23][C:24]([CH3:26])([CH3:25])[CH3:27])=[O:22])[CH2:19][CH2:20]4)[CH3:14])=[C:3]([O:2][CH3:1])[CH:12]=[CH:11][C:6]=3[C:7]\2=[O:10])=[N:29]1

Participants

5

Reactant 2

HCID 71278867HCID 71278867, compoundHCID 178520025HCID 178520025, compound

Product 1

HCID 178487199HCID 178487199, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

A solution of tert-butyl 4-[1-(6-methoxy-3-oxo-2,3-dihydrobenzofuran-7-yl)-ethyl]piperazine-1-carboxylate (0.091 g, 0.24 mmol) in methanol (3.0 mL) was added with 1H-indazole-3-carboxaldehyde (0.039 g, 0.27 mmol). Then, the mixture was added with 5 drops of piperidine, and then the mixture was stirred at 60° C. for 1 hour. The solvent was evaporated under reduced pressure, and then the residue was subjected to silica gel column chromatography (aminopropyl silica was used, eluted with chloroform/methanol (100:0→97:3)) to obtain tert-butyl (Z)-4-(1-{2-[(1H-indazol-3-yl)methylene]-6-methoxy-3-oxo-2,3-dihydrobenzofuran-7-yl}ethyl)piperazine-1-carboxylate (0.10 g, 85%).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. washthe residue was subjected to silica gel column chromatography (aminopropyl silica was used, eluted with chloroform/methanol (100:0→97:3))

Sources & evidence

ORD record
ord-21d27cd9b26841ae8e67e0cd89ad60a1
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

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