Piperidine → HCID 178487159, compound

HRID 1750012Notes

Reaction equation

HRID 1750012 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[C:13]#[C:14][C:15]([N:18]1[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH2:19]1)([CH3:17])[CH3:16].[NH:31]1[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[C:33]([CH:40]=O)=[N:32]1.N1CCCCC1>CO>[NH:31]1[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[C:33](/[CH:40]=[C:8]2\[O:9][C:5]3[C:4]([C:13]#[C:14][C:15]([N:18]4[CH2:19][CH2:20][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:22][CH2:23]4)([CH3:17])[CH3:16])=[C:3]([O:2][CH3:1])[CH:12]=[CH:11][C:6]=3[C:7]\2=[O:10])=[N:32]1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 71278755HCID 71278755, compoundHCID 178520025HCID 178520025, compound

Product 1

HCID 178487159HCID 178487159, compoundYield 91.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

A solution of tert-butyl 4-[4-(6-methoxy-3-oxo-2,3-dihydrobenzofuran-7-yl)-2-methylbut-3-yn-2-yl]piperazine-1-carboxylate (0.113 g, 0.273 mmol) in methanol (1 mL) was added with 1H-indazole-3-carboxaldehyde (0.0399 g, 0.273 mmol) and piperidine (0.0186 g, 0.218 mmol), and the mixture was stirred at 60° C. for 2 hours. The reaction mixture was concentrated, and the resulting residue was purified by silica gel column chromatography (chloroform/methanol) to obtain tert-butyl (Z)-4-(4-{2-[(1H-indazol-3-yl)methylene]-6-methoxy-3-oxo-2,3-dihydrobenzofuran-7-yl}-2-methylbut-3-yn-2-yl)piperazine-1-carboxylate (0.136 g, 91%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe resulting residue was purified by silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-b2f421c320d4473d96e9c52797adccbf
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

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