(1R,2R)-2-Aminocyclohexanol → 5-bromo-6-(4-chloro-phenyl)-pyrazine-2-carboxylic acid ((1R,2R)-2-hydroxy-cyclohexyl)-amide

HRID 1929843Notes

Reaction equation

HRID 1929843 reaction equation
[Br:1][C:2]1[N:3]=[CH:4][C:5]([C:15]([OH:17])=O)=[N:6][C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=1.[NH2:18][C@@H:19]1[CH2:24][CH2:23][CH2:22][CH2:21][C@H:20]1[OH:25]>>[OH:25][C@@H:20]1[CH2:21][CH2:22][CH2:23][CH2:24][C@H:19]1[NH:18][C:15]([C:5]1[CH:4]=[N:3][C:2]([Br:1])=[C:7]([C:8]2[CH:9]=[CH:10][C:11]([Cl:14])=[CH:12][CH:13]=2)[N:6]=1)=[O:17]

Participants

3

Reactant 2

HCID 735777(1R,2R)-2-AminocyclohexanolHCID 866169645-Bromo-6-(4-chloro-phenyl)-pyrazine-2-carboxylic acid

Product 1

HCID 866169725-bromo-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 19e, using 5-bromo-6-(4-chloro-phenyl)-pyrazine-2-carboxylic acid, and (1R,2R)-2-amino-cyclohexanol (commercially available) as starting materials to give the title compound as a light yellow solid, MS (ISP): 410.0, 412.0 (M+H)+.

Workup

  1. customThe title compound was synthesized in analogy to the procedure
  2. customdescribed for the preparation of Example 19e

Sources & evidence

ORD record
ord-e0d5fbd74a494528ba49821922abd578
Source dataset
uspto-grants-2012_05
Patent number
US08188093B2

Reaction notes

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