Water → HCID 86682033, compound

HRID 1749900Notes

Reaction equation

HRID 1749900 reaction equation
[OH:1][C:2]1[CH:29]=[CH:28][C:5]2[C:6](=[O:27])/[C:7](=[CH:9]/[C:10]3[C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[N:12]([CH2:19][O:20][CH2:21][CH2:22][Si:23]([CH3:26])([CH3:25])[CH3:24])[N:11]=3)/[O:8][C:4]=2[C:3]=1[CH2:30][N:31]1[CH2:36][CH2:35][N:34]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH2:33][CH2:32]1.C(=O)([O-])[O-].[K+].[K+].[O:50]1[CH2:54][CH2:53]OC1=O.O>CN(C=O)C>[OH:50][CH2:54][CH2:53][O:1][C:2]1[CH:29]=[CH:28][C:5]2[C:6](=[O:27])/[C:7](=[CH:9]/[C:10]3[C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[N:12]([CH2:19][O:20][CH2:21][CH2:22][Si:23]([CH3:25])([CH3:26])[CH3:24])[N:11]=3)/[O:8][C:4]=2[C:3]=1[CH2:30][N:31]1[CH2:36][CH2:35][N:34]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH2:33][CH2:32]1

Participants

6

Reactant 4

HCID 962WaterHCID 7303Ethylene carbonateHCID 11430Potassium CarbonateHCID 86682032HCID 86682032, compound

Product 1

HCID 86682033HCID 86682033, compoundYield 74.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of tert-butyl (Z)-4-({6-hydroxy-3-oxo-2-[(N-{[2-(trimethylsilyl)ethoxy]methyl}-1H-indazol-3-yl)methylene]-2,3-dihydrobenzofuran-7-yl}methyl)piperazine-1-carboxylate (0.416 g, 0.686 mmol) obtained in Step 2 in DMF (6 mL) was added with potassium carbonate (1.42 g, 10.3 mmol), and the mixture was stirred at room temperature for 10 minutes. The reaction mixture was added with 1,3-dioxolan-2-one (0.725 g, 8.23 mmol), and the mixture was stirred at 100° C. for 5 hours. The reaction mixture was cooled to room temperature, and then added with water (60 mL), and the mixture was vigorously stirred at room temperature for 30 minutes. The precipitated solid was collected by filtration to obtain tert-butyl (Z)-4-{[6-(2-hydroxyethoxy)-3-oxo-2-[(N-{[2-(trimethylsilyl)ethoxy]methyl}-1H-indazol-3-yl)methylene]-2,3-dihydrobenzofuran-7-yl]methyl}piperazine-1-carboxylate (0.331 g, 74%).

Workup

  1. stirringthe mixture was stirred at 100° C. for 5 hours
  2. temperatureThe reaction mixture was cooled to room temperature
  3. stirringthe mixture was vigorously stirred at room temperature for 30 minutes
  4. filtrationThe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-09eddb50294b44f9ba0fcbbbd3f6915c
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

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