3-Methanesulfonyl-5-(trifluoromethyl)benzoic acid → [(3-Methanesulfonyl-5-trifluoromethyl-benzoyl)-(2-methoxy-[3,4']bipyridinyl-3'-yl)-amino]-acetic acid methyl ester

HRID 878204Notes

Reaction equation

HRID 878204 reaction equation
CN(C)[S:3]([C:6]1[CH:7]=[C:8]([CH:31]=[C:32]([C:34]([F:37])([F:36])[F:35])[CH:33]=1)[C:9]([N:11]([CH2:26][C:27]([O:29][CH3:30])=[O:28])[C:12]1[CH:13]=[N:14][CH:15]=[CH:16][C:17]=1[C:18]1[C:19]([O:24][CH3:25])=[N:20][CH:21]=[CH:22][CH:23]=1)=[O:10])(=[O:5])=[O:4].[CH3:39]S(C1C=C(C=C(C(F)(F)F)C=1)C(O)=O)(=O)=O>>[CH3:30][O:29][C:27](=[O:28])[CH2:26][N:11]([C:9](=[O:10])[C:8]1[CH:31]=[C:32]([C:34]([F:37])([F:35])[F:36])[CH:33]=[C:6]([S:3]([CH3:39])(=[O:5])=[O:4])[CH:7]=1)[C:12]1[CH:13]=[N:14][CH:15]=[CH:16][C:17]=1[C:18]1[C:19]([O:24][CH3:25])=[N:20][CH:21]=[CH:22][CH:23]=1

Participants

3

Reactant 2

HCID 215445163-Methanesulfonyl-5-(trifluoromethyl)benzoic acidHCID 70663565Methyl 2-(3-(N,N-dimethylsulfamoyl)-N-(2-methoxy-3,4'-bipyridin-3'-yl)-5-(trifluoromethyl)benzamido)acetate

Product 1

HCID 70663544[(3-Methanesulfonyl-5-trifluoromethyl-benzoyl)-(2-methoxy-[3,4']bipyridinyl-3'-yl)-amino]-acetic acid methyl ester

Procedure

The title compound was prepared in analogy to example 90, from (2-methoxy-[3,4′]bipyridinyl-3′-ylamino)-acetic acid methyl ester (example 178, intermediate) and 3-methanesulfonyl-5-trifluoromethyl-benzoic acid (example 114, intermediate a) after a reaction time of 72 hours. The compound was purified by silica gel chromatography using a MPLC system (CombiFlash Companion, Isco Inc.) eluting with a gradient of n-heptane:EtOAc (100:0 to 20:80). The product-containing fractions were pooled and evaporated. The remaining solid was purified by preparative HPLC (Gemini NX column) with a gradient of methanol:water (containing 0.05% formic acid) (80:20 to 98:2). Light yellow foam (32%). MS (ESI): m/z=524.108 [M+H]+.

Workup

  1. customThe compound was purified by silica gel chromatography
  2. washeluting with a gradient of n-heptane:EtOAc (100:0 to 20:80)
  3. customevaporated
  4. customThe remaining solid was purified by preparative HPLC (Gemini NX column) with a gradient of methanol

Sources & evidence

ORD record
ord-6e099a71043b4ee4bfdfc1c5efd6a37d
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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