Potassium Carbonate → HCID 86757798, compound

HRID 1700289Notes

Reaction equation

HRID 1700289 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([NH:21][CH2:22][CH:23]=[CH:24][C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([C:31]#[N:32])[CH:26]=3)=[CH:17][C:16]=2[N+:33]([O-:35])=[O:34])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[K+].[K+].Br[CH2:43][C:44]([O:46][CH3:47])=[O:45]>CN(C=O)C.O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([N:21]([CH2:43][C:44]([O:46][CH3:47])=[O:45])[CH2:22][CH:23]=[CH:24][C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([C:31]#[N:32])[CH:26]=3)=[CH:17][C:16]=2[N+:33]([O-:35])=[O:34])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 86757799HCID 86757799, compound

Product 1

HCID 86757798HCID 86757798, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
55 °C

Procedure

To 4-(N′-(t-butoxycarbonyl)piperidin-4-yl)oxy-3-nitro-N-(3-(3-cyanophenyl)prop-2-en-1-yl)benzenamine (0.39 g) and K2CO3 (0.56 g) in DMF was added methyl bromoacetate. The mixture was stirred at 55° C. for 6 hours. The reaction was cooled, diluted with water and extracted with ethyl acetate (3×). The organic layer was concentrated and purified on silica gel column to afford 4-(N′-(t-butoxycarbonyl)piperidin-4-yl)oxy-3-nitro-N-(methoxycarbonylmethyl)-N-(3-(3-cyanophenyl)prop-2-en-1-yl)benzenamine (0.15 g).

Workup

  1. temperatureThe reaction was cooled
  2. extractionextracted with ethyl acetate (3×)
  3. concentrationThe organic layer was concentrated
  4. custompurified on silica gel column

Sources & evidence

ORD record
ord-4e524ded8b6f4e0a8ed1c8d6eaf21a26
Source dataset
uspto-grants-2002_02
Patent number
US06350761B1

Reaction notes

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