Hydrochloric Acid → HCID 59392368, compound

HRID 1512068Notes

Reaction equation

HRID 1512068 reaction equation
C[Si](C)(C)[N-][Si](C)(C)C.[Na+].[Cl:11][C:12]1[C:17]([Cl:18])=[CH:16][CH:15]=[C:14]([Cl:19])[C:13]=1[CH2:20][C:21]([NH:23][C:24]1[C:25]([C:30]([OH:32])=O)=[N:26][CH:27]=[CH:28][N:29]=1)=[O:22].O([CH2:41][CH:42]([F:44])[F:43])S(C(F)(F)F)(=O)=O.Cl>O1CCCC1>[F:43][CH:42]([F:44])[CH2:41][N:23]1[C:24]2=[N:29][CH:28]=[CH:27][N:26]=[C:25]2[C:30]([OH:32])=[C:20]([C:13]2[C:14]([Cl:19])=[CH:15][CH:16]=[C:17]([Cl:18])[C:12]=2[Cl:11])[C:21]1=[O:22]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 2724254Sodium bis(trimethylsilyl)amideHCID 27740892,2-Difluoroethyl trifluoromethanesulfonateHCID 59392367HCID 59392367, compound

Product 1

HCID 59392368HCID 59392368, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hexamethyldisilazide (“NaHMDS”) (1M in THF) (1.4 ml) was added dropwise to a solution of 3-[2-(2,3,6-trichloro-phenyl)-acetylamino]-pyrazine-2-carboxylic acid (Example 3.1) (0.225 g) in anhydrous tetrahydrofuran (10 ml) over a period of 10 minutes. Then difluoroethyl triflate (0.270 g) was added dropwise and the reaction mixture was allowed to stir at ambient temperature for 30 minutes. Then the reaction mixture was heated to reflux for 6 hours. The reaction mixture was allowed to cool to ambient temperature and acidified by addition of aqueous hydrochloric acid (1M). The mixture was concentrated. The residue was dissolved in diethyl ether and washed with aqueous hydrochloric acid (1M). The acid solution was extracted with ethyl acetate. The combined organic fractions were dried over magnesium sulfate and concentrated. The residue was purified by reverse phase HPLC to give Compound No. B11 of Table B (0.034 g).

Workup

  1. temperatureThen the reaction mixture was heated
  2. temperatureto reflux for 6 hours
  3. temperatureto cool to ambient temperature
  4. concentrationThe mixture was concentrated
  5. dissolutionThe residue was dissolved in diethyl ether
  6. washwashed with aqueous hydrochloric acid (1M)
  7. extractionThe acid solution was extracted with ethyl acetate
  8. dry with materialThe combined organic fractions were dried over magnesium sulfate
  9. concentrationconcentrated
  10. customThe residue was purified by reverse phase HPLC
  11. customto give Compound No

Sources & evidence

ORD record
ord-966ea3408dd34be8b68bb5f7725f8091
Source dataset
uspto-grants-2012_07
Patent number
US08217055B2

Reaction notes

Loading…