6-(3-chloro-phenyl)-5-(2,2,2-trifluoro-ethoxy)-3-trifluoromethyl-pyrazine-2-carboxylic acid ((1 R,2R)-2-hydroxy-cyclohexyl)-amide → 6-(3,4-dichloro-phenyl)-5-(2,2,2-trifluoro-ethoxy)-3-trifluoromethyl-pyrazine-2-carboxylic acid ((1R,2R)-2-hydroxy-cyclohexyl)-amide

HRID 416479Notes

Reaction equation

HRID 416479 reaction equation
[OH:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@H:3]1[NH:8][C:9]([C:11]1[C:16]([C:17]([F:20])([F:19])[F:18])=[N:15][C:14]([O:21][CH2:22][C:23]([F:26])([F:25])[F:24])=[C:13]([C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([Cl:33])[CH:28]=2)[N:12]=1)=[O:10].COC(C1C(C(F)(F)F)=NC(Br)=C(C2C=CC([Cl:55])=C(Cl)C=2)N=1)=O>>[OH:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@H:3]1[NH:8][C:9]([C:11]1[C:16]([C:17]([F:18])([F:19])[F:20])=[N:15][C:14]([O:21][CH2:22][C:23]([F:26])([F:25])[F:24])=[C:13]([C:27]2[CH:32]=[CH:31][C:30]([Cl:55])=[C:29]([Cl:33])[CH:28]=2)[N:12]=1)=[O:10]

Participants

3

Reactant 2

HCID 444634636-(3-chloro-phenyl)-5-(2,2,2-trifluoro-ethoxy)-3-trifluoromethyl-pyrazine-2-carboxylic acid ((1 R,2R)-2-hydroxy-cyclohexyl)-amideHCID 866347085-Bromo-6-(3,4-dichloro-phenyl)-3-trifluoromethyl-pyrazine-2-carboxylic acid methyl ester

Product 1

HCID 444665726-(3,4-dichloro-phenyl)-5-(2,2,2-trifluoro-ethoxy)-3-trifluoromethyl-pyrazine-2-carboxylic acid ((1R,2R)-2-hydroxy-cyclohexyl)-amide

Procedure

In analogy to example 4 (6-(3-chloro-phenyl)-5-(2,2,2-trifluoro-ethoxy)-3-trifluoromethyl-pyrazine-2-carboxylic acid ((1R,2R)-2-hydroxy-cyclohexyl)-amide) the title compound was prepared by substituting 5-bromo-6-(3-chloro-phenyl)-3-trifluoromethyl-pyrazine-2-carboxylic acid methyl ester with 5-bromo-6-(3,4-dichloro-phenyl)-3-trifluoromethyl-pyrazine-2-carboxylic acid methyl ester.

Sources & evidence

ORD record
ord-39c2adca83b9476d931d6509703fca08
Source dataset
uspto-grants-2012_01
Patent number
US08088920B2

Reaction notes

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