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

HRID 1099551Notes

Reaction equation

HRID 1099551 reaction equation
[NH2:1][CH2:2][CH2:3][OH:4].[CH:5]1([C:8]2[CH:32]=[CH:31][C:11](/[CH:12]=[C:13]3\[N:14]=[C:15]([C:19]4[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][CH:28]5[CH2:30][CH2:29]5)=[CH:21][CH:20]=4)[O:16][C:17]\3=[O:18])=[CH:10][CH:9]=2)[CH2:7][CH2:6]1>C(O)C>[CH:28]1([CH2:27][CH2:26][O:25][C:22]2[CH:23]=[CH:24][C:19]([C:15]([NH:14]/[C:13](/[C:17]([NH:1][CH2:2][CH2:3][OH:4])=[O:18])=[CH:12]\[C:11]3[CH:31]=[CH:32][C:8]([CH:5]4[CH2:6][CH2:7]4)=[CH:9][CH:10]=3)=[O:16])=[CH:20][CH:21]=2)[CH2:30][CH2:29]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

2-Aminoethanol (20 μL, 0.33 mmol) was added to a solution of ethanol (1.6 mL) containing (4Z)-4-(4-cyclopropylbenzylidene)-2-[4-(2-cyclopropylethoxy)phenyl]-1,3-oxazol-5(4H)-one (95 mg, 0.25 mmol) prepared in Example 9 (9c). The mixture was stirred at 60° C. for 1 hour, and then the solvent was removed. The residue was washed with 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 removed
  2. washThe residue was washed with hexane:ethyl acetate (3:1
  3. filtrationThe precipitate was collected by filtration
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-25a59feabb954b6990544834f381c9b1
Source dataset
uspto-grants-2012_03
Patent number
US08143446B2

Reaction notes

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