Ethanolamine → 4-(2-Cyclopropylethoxy)-N-((Z)-2-(4-cyclopropylphenyl)-1-{[(2-hydroxyethyl)amino]carbonyl}vinyl)benzamide

HRID 1799230Notes

Reaction equation

HRID 1799230 reaction equation
[CH:1]1([C:4]2[CH:28]=[CH:27][C:7](/[CH:8]=[C:9]3\[N:10]=[C:11]([C:15]4[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH2:23][CH:24]5[CH2:26][CH2:25]5)=[CH:17][CH:16]=4)[O:12][C:13]\3=[O:14])=[CH:6][CH:5]=2)[CH2:3][CH2:2]1.[NH2:29][CH2:30][CH2:31][OH:32]>C(O)C>[CH:24]1([CH2:23][CH2:22][O:21][C:18]2[CH:19]=[CH:20][C:15]([C:11]([NH:10]/[C:9](/[C:13]([NH:29][CH2:30][CH2:31][OH:32])=[O:14])=[CH:8]\[C:7]3[CH:27]=[CH:28][C:4]([CH:1]4[CH2:2][CH2:3]4)=[CH:5][CH:6]=3)=[O:12])=[CH:16][CH:17]=2)[CH2:26][CH2:25]1

Participants

4

Reactant 2

HCID 700EthanolamineHCID 66812352(4Z)-4-(4-Cyclopropylbenzylidene)-2-[4-(2-cyclopropylethoxy)phenyl]-1,3-oxazol-5(4H)-one

Product 1

HCID 576845604-(2-Cyclopropylethoxy)-N-((Z)-2-(4-cyclopropylphenyl)-1-{[(2-hydroxyethyl)amino]carbonyl}vinyl)benzamideYield 87.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

To an ethanol (1.6 mL) solution of (4Z)-4-(4-cyclopropylbenzylidene)-2-[4-(2-cyclopropylethoxy)phenyl]-1,3-oxazol-5(4H)-one (95 mg, 0.25 mmol) prepared in Example 1 (1c) was added 2-aminoethanol (20 μL, 0.33 mmol), and the mixture was stirred at 60° C. for one hour. The solvent was evaporated, and the residue was washed with n-hexane:ethyl acetate (3:1, V/V). The precipitate was collected by filtration and dried under reduced pressure to give 95 mg of the title compound (white powder, yield: 86%).

Workup

  1. customThe solvent was evaporated
  2. washthe residue was washed with n-hexane:ethyl acetate (3:1, V/V)
  3. filtrationThe precipitate was collected by filtration
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-27bd43c75106486d90fbe73e998b1947
Source dataset
uspto-grants-2013_01
Patent number
US08344029B2

Reaction notes

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