Piconol → 6-(3-chloro-phenyl)-5-(pyridin-2-ylmethoxy)-3-trifluoromethyl-pyrazine-2-carboxylic acid ((1R,2R)-2-hydroxy-cyclohexyl)-amide

HRID 416478Notes

Reaction equation

HRID 416478 reaction equation
O[C@@H]1CCCC[C@H]1NC(C1C(C(F)(F)F)=N[C:14]([O:21]CC2CC2)=[C:13]([C:26]2[CH:31]=[CH:30][C:29](Cl)=CC=2)[N:12]=1)=O.[OH:33][C@@H:34]1[CH2:39][CH2:38][CH2:37][CH2:36][C@H:35]1[NH:40][C:41]([C:43]1[C:48]([C:49]([F:52])([F:51])[F:50])=[N:47][C:46](Br)=[C:45]([C:54]2[CH:59]=[CH:58][CH:57]=[C:56]([Cl:60])[CH:55]=2)[N:44]=1)=[O:42].C1(CO)CC1.N1C=CC=CC=1CO>>[OH:33][C@@H:34]1[CH2:39][CH2:38][CH2:37][CH2:36][C@H:35]1[NH:40][C:41]([C:43]1[C:48]([C:49]([F:52])([F:51])[F:50])=[N:47][C:46]([O:21][CH2:14][C:13]2[CH:26]=[CH:31][CH:30]=[CH:29][N:12]=2)=[C:45]([C:54]2[CH:59]=[CH:58][CH:57]=[C:56]([Cl:60])[CH:55]=2)[N:44]=1)=[O:42]

Participants

5

Reactant 4

HCID 11474PiconolHCID 75644CyclopropanemethanolHCID 444665706-(4-chloro-phenyl)-5-cyclopropylmethoxy-3-trifluoromethyl-pyrazine-2-carboxylic acid ((1R,2R)-2-hydroxy-cyclohexyl)-amideHCID 866347055-bromo-6-(3-chloro-phenyl)-3-trifluoromethyl-pyrazine-2-carboxylic acid ((1R,2R)-2-hydroxy-cyclohexyl)-amide

Product 1

HCID 444634606-(3-chloro-phenyl)-5-(pyridin-2-ylmethoxy)-3-trifluoromethyl-pyrazine-2-carboxylic acid ((1R,2R)-2-hydroxy-cyclohexyl)-amide

Procedure

In analogy to example 1 (6-(4-chloro-phenyl)-5-cyclopropylmethoxy-3-trifluoromethyl-pyrazine-2-carboxylic acid ((1R,2R)-2-hydroxy-cyclohexyl)-amide) this compound was prepared by substituting 5-bromo-6-(4-chloro-phenyl)-3-trifluoromethyl-pyrazine-2-carboxylic acid ((1R,2R)-2-hydroxy-cyclohexyl)-amide with 5-bromo-6-(3-chloro-phenyl)-3-trifluoromethyl-pyrazine-2-carboxylic acid ((1R,2R)-2-hydroxy-cyclohexyl)-amide and cyclopropylmethanol with pyridin-2-yl-methanol.

Sources & evidence

ORD record
ord-bbbde96156914d04a01467967dd8983d
Source dataset
uspto-grants-2012_01
Patent number
US08088920B2

Reaction notes

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