Ethyl trifluoromethanesulphonate → HCID 59623724, compound

HRID 1093945Notes

Reaction equation

HRID 1093945 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:10]([NH:11][S:12]([CH2:15][C:16]2[CH:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:19]=[CH:18][C:17]=2[Cl:26])(=[O:14])=[O:13])=[N:9][CH:8]=[CH:7][N:6]=1)=[O:4].[CH:27](N(CC)C(C)C)(C)[CH3:28].C(OS(C(F)(F)F)(=O)=O)C>C(#N)C>[CH3:1][O:2][C:3]([C:5]1[C:10]([N:11]([S:12]([CH2:15][C:16]2[CH:21]=[C:20]([C:22]([F:25])([F:23])[F:24])[CH:19]=[CH:18][C:17]=2[Cl:26])(=[O:13])=[O:14])[CH2:27][CH3:28])=[N:9][CH:8]=[CH:7][N:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 67924Ethyl trifluoromethanesulphonateHCID 81531DiisopropylethylamineHCID 59623721HCID 59623721, compound

Product 1

HCID 59623724HCID 59623724, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a solution of 3-(2-chloro-5-trifluoromethyl-phenylmethanesulfonylamino)-pyrazine-2-carboxylic acid methyl ester (Example 2.1) (1.5 g) in acetonitrile (20 ml) was added N,N-diisopropylethylamine (“Hunig's base”) (0.71 ml) at ambient temperature. The mixture was stirred for 5 minutes at ambient temperature before dropwise addition of a solution of ethyltrifluoromethanesulfonate (0.71 ml) in acetonitrile (5 ml) at ambient to temperature. The reaction mixture was stirred at ambient temperature for 4 hours. The reaction mixture was concentrated and the residue purified by column chromatography on silica gel (eluent: dichloromethane) to give 3-[(2-chloro-5-trifluoromethyl-phenyl-methanesulfonyl)-ethyl-amino]-pyrazine-2-carboxylic acid methyl ester as a beige solid (0.968 g). 1H-NMR (400 MHz, CDCl3): 8.57 (d, 1H), 8.52 (d, 1H), 7.77 (m, 1H), 7.50-7.56 (m, 2H), 4.64 (m, 2H), 4.01 (q, 2H), 4.00 (s, 3H), 1.23 (t, 3H) ppm.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue purified by column chromatography on silica gel (eluent: dichloromethane)

Sources & evidence

ORD record
ord-1d86ff2072be40fcafd87033f5f466a2
Source dataset
uspto-grants-2012_03
Patent number
US08133849B2

Reaction notes

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