Potassium Carbonate → HCID 66788709, compound

HRID 1045642Notes

Reaction equation

HRID 1045642 reaction equation
C([O:3][C:4]([C:6]1[C:11]([CH:12]([S:15]([CH2:18][C:19]2[C:24]([C:25]([F:28])([F:27])[F:26])=[CH:23][CH:22]=[CH:21][C:20]=2[Cl:29])(=[O:17])=[O:16])[CH2:13][CH3:14])=[N:10][CH:9]=[CH:8][N:7]=1)=O)C.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[Cl:29][C:20]1[CH:21]=[CH:22][CH:23]=[C:24]([C:25]([F:27])([F:26])[F:28])[C:19]=1[C:18]1[S:15](=[O:17])(=[O:16])[CH:12]([CH2:13][CH3:14])[C:11]2[N:10]=[CH:9][CH:8]=[N:7][C:6]=2[C:4]=1[OH:3]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 66788563HCID 66788563, compound

Product 1

HCID 66788709HCID 66788709, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 3-[1-(2-chloro-6-trifluoromethyl-phenylmethanesulfonyl)-propyl]-pyrazine-2-carboxylic acid ethyl ester (0.106 g) and potassium carbonate (0.081 g) in N,N-dimethylformamide (2 ml) was heated to 120° C. for 1 hour. The reaction mixture was cooled to ambient temperature, diluted with water and washed with diethyl ether. The aqueous layer was acidified with aqueous hydrochloric acid (2M) and extracted with ethyl acetate (2×20 ml). The organic layer was concentrated and the residue purified by reverse phase chromatography (eluent: 0-100% v/v acetonitrile in water with 0.05% trifluoroacetic acid) to give 7-(2-chloro-6-trifluoromethyl-phenyl)-5-ethyl-6,6-dioxo-5,6-dihydro-6-thia-1,4-diaza-naphthalen-8-ol Compound No. E1 of Table E (0.042 g). MH+=405, RT=1.38 min.

Workup

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. washwashed with diethyl ether
  3. extractionextracted with ethyl acetate (2×20 ml)
  4. concentrationThe organic layer was concentrated
  5. customthe residue purified by reverse phase chromatography (eluent: 0-100% v/v acetonitrile in water with 0.05% trifluoroacetic acid)

Sources & evidence

ORD record
ord-3bc9fe59e5ed4ba18b3ca36668343cd3
Source dataset
uspto-grants-2013_10
Patent number
US08569301B2

Reaction notes

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