Hydrochloric Acid → [6-Chloro-3-(2.2-difluoro-2-pyridin-2-yl-ethylamino)-2-oxo-2H-pyrazin 1-yl]-acetic Acid

HRID 1795291Notes

Reaction equation

HRID 1795291 reaction equation
C([O:3][C:4](=[O:25])[CH2:5][N:6]1[C:11]([Cl:12])=[CH:10][N:9]=[C:8]([NH:13][CH2:14][C:15]([F:23])([F:22])[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)[C:7]1=[O:24])C.[OH-].[K+].Cl.[Cl-].[K+]>CO>[Cl:12][C:11]1[N:6]([CH2:5][C:4]([OH:25])=[O:3])[C:7](=[O:24])[C:8]([NH:13][CH2:14][C:15]([F:22])([F:23])[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)=[N:9][CH:10]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 4873Potassium ChlorideHCID 14797Potassium HydroxideHCID 11211001[6-Chloro-3-(2,2-difluoro-2-pyridin-2-yl-ethylamino)-2-oxo-2H-pyrazin-1-yl]-acetic Acid Ethyl Ester

Product 1

HCID 10936874[6-Chloro-3-(2.2-difluoro-2-pyridin-2-yl-ethylamino)-2-oxo-2H-pyrazin 1-yl]-acetic Acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 7.27 g (19.5 mmol) of [6-chloro-3-(2,2-difluoro-2-pyridin-2-yl-ethylamino)-2-oxo-2H-pyrazin-1-yl]-acetic acid ethyl ester in 200 mL of methanol was added 39 mL (39.0 mmol) of 1M aq. potassium hydroxide. After 3 h the solution was acidified to pH=7 using conc. HCl, and concentrated at reduced pressure (azeotrope with PhCH3) to give a white solid containing potassium chloride and the product. 1H NMR (CD3OD) δ 8.64 (d, 1H, 4.8 Hz), 7.93 (ddd,1H, 7.7, 7.7, 1.5 Hz), 7.70 (d, 1H, 8.0 Hz), 7.49 (dd, 1H, 5.2, 7.4 Hz), 6.80 (s, 1H), 4.67 (s, 2H), 4.27 (t, 2H, 13.9 Hz).

Workup

  1. concentrationconcentrated at reduced pressure (azeotrope with PhCH3)
  2. customto give a white solid

Sources & evidence

ORD record
ord-65d8299fdc6349a58082d893053d50da
Source dataset
uspto-grants-2006_04
Patent number
US07026324B2

Reaction notes

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