2-Chlorophenol → 5-(2-Chloro-phenoxy)-6-(4-chloro-phenyl)-pyrazine-2-carboxylic acid ((1R,2R)-2-hydroxy-cyclohexyl)-amide

HRID 1929844Notes

Reaction equation

HRID 1929844 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[CH:16]=[N:15][C:14](Br)=[C:13]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)[N:12]=1)=[O:10].[Cl:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[OH:32]>>[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[CH:16]=[N:15][C:14]([O:32][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=2[Cl:25])=[C:13]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)[N:12]=1)=[O:10]

Participants

3

Reactant 2

HCID 72452-ChlorophenolHCID 866169725-bromo-6-(4-chloro-phenyl)-pyrazine-2-carboxylic acid ((1R,2R)-2-hydroxy-cyclohexyl)-amide

Product 1

HCID 248572485-(2-Chloro-phenoxy)-6-(4-chloro-phenyl)-pyrazine-2-carboxylic acid ((1R,2R)-2-hydroxy-cyclohexyl)-amide

Procedure

The title compound was synthesized in analogy to the procedure described for the preparation of Example 36 c, using 5-bromo-6-(4-chloro-phenyl)-pyrazine-2-carboxylic acid ((1R,2R)-2-hydroxy-cyclohexyl)-amide, and chlorophenol (commercially available) as starting materials to give the title compound as a white solid. mp.: 154-155° C., MS (ISP): 458.3, 460.3 (M+H)+.

Workup

  1. customThe title compound was synthesized in analogy to the procedure
  2. customdescribed for the preparation of Example 36 c

Sources & evidence

ORD record
ord-2785ad4a601443e580f41d1a38602d1e
Source dataset
uspto-grants-2012_05
Patent number
US08188093B2

Reaction notes

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