2,6-Bis(trifluoromethyl)pyridine-4-carboxylic acid → Methyl 2-(N-(2-methoxy-3,4'-bipyridin-3'-yl)-2,6-bis(trifluoromethyl)isonicotinamido)acetate

HRID 878205Notes

Reaction equation

HRID 878205 reaction equation
CN(C)S(C1C=C(C=C(C(F)(F)F)C=1)C([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)(=O)=O.[F:39][C:40]([F:55])([F:54])[C:41]1[CH:42]=[C:43]([CH:47]=[C:48]([C:50]([F:53])([F:52])[F:51])[N:49]=1)[C:44]([OH:46])=O>>[CH3:25][O:24][C:19]1[C:18]([C:17]2[CH:16]=[CH:15][N:14]=[CH:13][C:12]=2[N:11]([CH2:26][C:27]([O:29][CH3:30])=[O:28])[C:44](=[O:46])[C:43]2[CH:47]=[C:48]([C:50]([F:53])([F:52])[F:51])[N:49]=[C:41]([C:40]([F:39])([F:55])[F:54])[CH:42]=2)=[CH:23][CH:22]=[CH:21][N:20]=1

Participants

3

Reactant 2

HCID 306891352,6-Bis(trifluoromethyl)pyridine-4-carboxylic acidHCID 70663565Methyl 2-(3-(N,N-dimethylsulfamoyl)-N-(2-methoxy-3,4'-bipyridin-3'-yl)-5-(trifluoromethyl)benzamido)acetate

Product 1

HCID 86670785Methyl 2-(N-(2-methoxy-3,4'-bipyridin-3'-yl)-2,6-bis(trifluoromethyl)isonicotinamido)acetate

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 2,6-bis(trifluoromethyl)isonicotinic acid (Key Organics Ltd.) after a reaction time of 48 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). Light yellow solid (55%). MS (ESI): m/z=515.114 [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)

Sources & evidence

ORD record
ord-b219f95604d84b69a51ad5e92678c62b
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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