Diisopropylethylamine → 3-Methanesulfonyl-N-(2-methanesulfonyl-ethyl)-N-[4-(2-trifluoromethoxy-phenyl)-pyridin-3-yl]-5-trifluoromethyl-benzamide

HRID 878357Notes

Reaction equation

HRID 878357 reaction equation
[CH3:1][S:2]([CH2:5][CH2:6][NH:7][C:8]1[CH:9]=[N:10][CH:11]=[CH:12][C:13]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[O:20][C:21]([F:24])([F:23])[F:22])(=[O:4])=[O:3].CCN(C(C)C)C(C)C.FC1C=CC=C(OC)C=1C1C=CN=CC=1N(CC(F)(F)F)[C:50](=[O:65])[C:51]1[CH:56]=[C:55]([C:57]([F:60])([F:59])[F:58])[CH:54]=[C:53]([S:61]([CH3:64])(=[O:63])=[O:62])[CH:52]=1>C(Cl)Cl>[CH3:64][S:61]([C:53]1[CH:52]=[C:51]([CH:56]=[C:55]([C:57]([F:58])([F:59])[F:60])[CH:54]=1)[C:50]([N:7]([CH2:6][CH2:5][S:2]([CH3:1])(=[O:4])=[O:3])[C:8]1[CH:9]=[N:10][CH:11]=[CH:12][C:13]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[O:20][C:21]([F:23])([F:24])[F:22])=[O:65])(=[O:63])=[O:62]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 70663444(2-Methanesulfonyl-ethyl)-[4-(2-trifluoromethoxy-phenyl)-pyridin-3-yl]-amineHCID 86670807N-[4-(2-Fluoro-6-methoxy-phenyl)-pyridin-3-yl]-3-methanesulfonyl-N-(2,2,2-trifluoro-ethyl)-5-trifluoromethyl-benzamide2×

Product 1

HCID 866708213-Methanesulfonyl-N-(2-methanesulfonyl-ethyl)-N-[4-(2-trifluoromethoxy-phenyl)-pyridin-3-yl]-5-trifluoromethyl-benzamideYield 13%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared in analogy to example 72, intermediate, from (2-methanesulfonyl-ethyl)-[4-(2-trifluoromethoxy-phenyl)-pyridin-3-yl]-amine, DIPEA and 3-methanesulfonyl-5-trifluoromethyl-benzoyl chloride (example 223, intermediate d) in CH2Cl2 after a reaction time of 12 hours at 25° C. The crude thus obtained was purified by preparative HPLC (ammonium acetate/acetonitrile) to furnish the title compound as an off-white solid (15 mg, 13%). MS (ESI): m/z=611.2 [M+H]+.

Workup

  1. customThe crude thus obtained
  2. customwas purified by preparative HPLC (ammonium acetate/acetonitrile)

Sources & evidence

ORD record
ord-f59ac56a6a114310aa0a59db660480f0
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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