Diisopropylethylamine → HCID 59623750, compound

HRID 1093947Notes

Reaction equation

HRID 1093947 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].C(N(CC)C(C)C)(C)C.[Cl:36][CH:37]([Cl:47])[CH2:38]OS(C(F)(F)F)(=O)=O>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])[CH2:38][CH:37]([Cl:47])[Cl:36])=[N:9][CH:8]=[CH:7][N:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 59623721HCID 59623721, compoundHCID 59623751HCID 59623751, compound

Product 1

HCID 59623750HCID 59623750, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 3-(2-chloro-5-trifluoromethyl-phenylmethanesulfonylamino)-pyrazine-2-carboxylic acid methyl ester (Example 2.1) (0.5 g) in acetonitrile (5 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 2,2-dichloroethyltrifluoromethanesulfonate (0.603 g) at ambient temperature. The reaction mixture was stirred at ambient temperature for 20 hours. The reaction mixture was concentrated and the residue purified by column chromatography on silica gel (eluent: iso-hexane/ethyl acetate 4:1) to give 3-[(2-chloro-5-trifluoromethyl-phenylmethanesulfonyl)-(2,2-dichloro-ethyl)-amino]-pyrazine-2-carboxylic acid methyl ester as a white solid (0.179 g). 1H-NMR (400 MHz, CDCl3): 8.61 (d, 1H), 8.51 (d, 1H), 7.73 (s, 1H), 7.53-7.59 (m, 2H), 5.99-6.02 (m, 1H), 4.71 (s, 2H), 4.58 (d, 2H), 4.02 (s, 3H) ppm.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue purified by column chromatography on silica gel (eluent: iso-hexane/ethyl acetate 4:1)

Sources & evidence

ORD record
ord-6a7d9a2b064a4fa3ac14032c58838d27
Source dataset
uspto-grants-2012_03
Patent number
US08133849B2

Reaction notes

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