Potassium Acetate → HCID 178494125, compound

HRID 706002Notes

Reaction equation

HRID 706002 reaction equation
Cl.[Cl:2][C:3]1[CH:20]=[CH:19][C:6]([O:7][C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][C:16](=[NH:18])[NH2:17])=[CH:10][CH:9]=2)=[CH:5][C:4]=1[C:21]([F:24])([F:23])[F:22].[OH:25][CH:26]=[C:27]([CH2:32][C:33]1[CH:34]=[N:35][C:36]([O:39][CH3:40])=[N:37][CH:38]=1)[C:28](OC)=O.C([O-])(=O)C.[K+]>C1(C)C=CC=CC=1>[Cl:2][C:3]1[CH:20]=[CH:19][C:6]([O:7][C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][C:16]3[NH:17][CH:28]=[C:27]([CH2:32][C:33]4[CH:34]=[N:35][C:36]([O:39][CH3:40])=[N:37][CH:38]=4)[C:26](=[O:25])[N:18]=3)=[CH:10][CH:9]=2)=[CH:5][C:4]=1[C:21]([F:22])([F:23])[F:24]

Participants

5

Reactant 3

HCID 517044Potassium AcetateHCID 67773588Methyl 3-hydroxy-2-((2-methoxypyrimidin-5-yl)methyl)acrylateHCID 677756383-(4-(4-Chloro-3-(trifluoromethyl)phenoxy)phenyl)propanimidamide hydrochloride

Product 1

HCID 178494125HCID 178494125, compoundYield 42.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The suspension of 3-(4-(4-chloro-3-(trifluoromethyl)phenoxy)phenyl)propanimidamide hydrochloride (5.9 g, 15.56 mmol), methyl 3-hydroxy-2-((2-methoxypyrimidin-5-yl)methyl)acrylate (3.49 g, 15.56 mmol) and potassium acetate (4.58 g, 46.7 mmol) in toluene (100 mL) was heated under reflux overnight. Dean-Stark apparatus was used to remove water formed in the reaction. The residue was recrystallized in ethyl acetate and washed with ether to provide the title compound (3.4 g, 42%). LCMS: rt=1.71 min, [M+H+]=517

Workup

  1. temperaturewas heated
  2. temperatureunder reflux overnight
  3. customto remove water
  4. customformed in the reaction
  5. customThe residue was recrystallized in ethyl acetate
  6. washwashed with ether

Sources & evidence

ORD record
ord-aa43a47642d940aba5bc945523f33e5b
Source dataset
uspto-grants-2015_11
Patent number
US09174968B2

Reaction notes

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