Hydrochloric Acid → 3-Amino-6-chloro-5-trifluoromethyl-pyrazine-2-carboxylic acid

HRID 2173736Notes

Reaction equation

HRID 2173736 reaction equation
C([O:3][C:4]([C:6]1[C:11]([NH2:12])=[N:10][C:9]([C:13]([F:16])([F:15])[F:14])=[C:8]([Cl:17])[N:7]=1)=[O:5])C.[OH-].[Na+].O.Cl>C(O)C>[NH2:12][C:11]1[C:6]([C:4]([OH:5])=[O:3])=[N:7][C:8]([Cl:17])=[C:9]([C:13]([F:14])([F:16])[F:15])[N:10]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 894432453-Amino-6-chloro-5-trifluoromethyl-pyrazine-2-carboxylic acid ethyl ester2×

Product 1

HCID 894432623-Amino-6-chloro-5-trifluoromethyl-pyrazine-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirring solution of 3-amino-6-chloro-5-trifluoromethyl-pyrazine-2-carboxylic acid ethyl ester (Intermediate 7A) (165 mg, 0.612 mmol) in dry ethanol (10 ml), 2M NaOH (0.306 ml, 0.612 mmol) was added. After stirring at RT for 10 minutes, the reaction mixture was poured into water (30 ml) and the pH taken to 6 with the addition of 1M HCl. The product was extracted with EtOAc (2×30 ml). The organics were combined and washed with brine (20 ml), dried (MgSO4) and concentrated in vacuo. The crude material was purified by preparative LC-MS using 0.1% TFA/MeCN/Water system to afford the title compound. MS m/z 244 [M+H]+

Workup

  1. extractionThe product was extracted with EtOAc (2×30 ml)
  2. washwashed with brine (20 ml)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe crude material was purified by preparative LC-MS

Sources & evidence

ORD record
ord-5d678ea3d1ed40f1ab5123dde4478aa8
Source dataset
uspto-grants-2015_06
Patent number
US09056867B2

Reaction notes

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