Cesium carbonate → HCID 178494147, compound

HRID 474864Notes

Reaction equation

HRID 474864 reaction equation
[C:1](=[NH:25])([O:3][CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([O:20][C:21]([F:24])([F:23])[F:22])[CH:14]=2)=[CH:8][CH:7]=1)[NH2:2].[OH:26]/[CH:27]=[C:28](/[CH2:33][C:34]1[CH:35]=[N:36][C:37]([O:40][CH3:41])=[N:38][CH:39]=1)\[C:29](OC)=O.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1>[Cl:19][C:16]1[CH:17]=[CH:18][C:13]([O:12][C:9]2[CH:8]=[CH:7][C:6]([CH2:5][CH2:4][O:3][C:1]3[NH:2][CH:29]=[C:28]([CH2:33][C:34]4[CH:35]=[N:36][C:37]([O:40][CH3:41])=[N:38][CH:39]=4)[C:27](=[O:26])[N:25]=3)=[CH:11][CH:10]=2)=[CH:14][C:15]=1[O:20][C:21]([F:24])([F:22])[F:23]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 67773579(Z)-methyl 3-hydroxy-2-((2-methoxypyrimidin-5-yl)methyl)acrylateHCID 679535154-(4-Chloro-3-(trifluoromethoxy)phenoxy)phenethyl carbamimidate

Product 1

HCID 178494147HCID 178494147, compoundYield 15.83%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The same procedure as E177 from 4-(4-chloro-3-(trifluoromethoxy)phenoxy)phenethyl carbamimidate (100 mg, 0.267 mmol), (Z)-methyl 3-hydroxy-2((2-methoxypyrimidin-5-yl) methyl)acrylate (180 mg, 0.803 mmol) and Cs2CO3 (260 mg, 0.798 mmol) in 1,4-dioxane (2 mL), except that the reaction temperature was 120° C. and the time was 4 h, to afford the title compound (28 mg, 0.042 mmol, 15.83% yield). LCMS: rt=3.63 min, [M+H+]=549

Workup

  1. customwas 120° C.

Sources & evidence

ORD record
ord-eb65326146444d9196ba465d13b2340d
Source dataset
uspto-grants-2014_01
Patent number
US08637536B2

Reaction notes

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