Hydrochloric Acid → HCID 66789409, compound

HRID 1045637Notes

Reaction equation

HRID 1045637 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:10]([CH2:11]Br)=[N:9][CH:8]=[CH:7][N:6]=1)=[O:4].Br.[Cl:14][C:15]1[C:25]([Cl:26])=[CH:24][CH:23]=[C:22]([F:27])[C:16]=1[CH2:17][S:18]C(=N)N.C(=O)([O-])[O-].[K+].[K+].Cl>C(#N)C>[CH3:1][O:2][C:3]([C:5]1[C:10]([CH2:11][S:18][CH2:17][C:16]2[C:22]([F:27])=[CH:23][CH:24]=[C:25]([Cl:26])[C:15]=2[Cl:14])=[N:9][CH:8]=[CH:7][N:6]=1)=[O:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 66788396HCID 66788396, compoundHCID 66788626HCID 66788626, compound

Product 1

HCID 66789409HCID 66789409, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of 3-bromomethyl-pyrazine-2-carboxylic acid methyl ester (2.5 g) and 2-(2,3-dichloro-6-fluoro-benzyl)-isothiourea hydrobromide (2.75 g) in acetonitrile (20 ml) was added potassium carbonate (3.8 g). The reaction mixture was stirred at ambient temperature for 5 hours, then stored at ambient temperature for 16 hours. The reaction mixture was poured into aqueous hydrochloric acid (2M) and extracted with ethyl acetate. The phases were separated and the organic layer was washed with saturated aqueous sodium hydrogen carbonate (saturated) and brine. The organic layer was concentrated and the residue purified by chromatography on silica gel (eluent: 0-10% v/v ethyl acetate in hexane) to give Compound No. A1 of Table A (0.26 g). 1H-NMR (400 MHz, CDCl3): 8.63 (d, 1H), 8.59 (d, 1H), 7.30-7.34 (m, 1H), 6.91-6.95 (m, 1H), 4.37 (m, 2H), 4.00 (s, 3H), 3.99 (m, 2H) ppm.

Workup

  1. waitstored at ambient temperature for 16 hours
  2. extractionextracted with ethyl acetate
  3. customThe phases were separated
  4. washthe organic layer was washed with saturated aqueous sodium hydrogen carbonate (saturated) and brine
  5. concentrationThe organic layer was concentrated
  6. customthe residue purified by chromatography on silica gel (eluent: 0-10% v/v ethyl acetate in hexane)
  7. customto give Compound No

Sources & evidence

ORD record
ord-493cd86062594e319cd90ad204012ffe
Source dataset
uspto-grants-2013_10
Patent number
US08569301B2

Reaction notes

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