N-methyl-4-o-tolylpyridin-3-amine → {3-[Methyl-(4-o-tolyl-pyridin-3-yl)-carbamoyl]-5-trifluoromethyl-phenyl}-carbamic acid tert-butyl ester

HRID 878185Notes

Reaction equation

HRID 878185 reaction equation
[CH3:1][NH:2][C:3]1[CH:4]=[N:5][CH:6]=[CH:7][C:8]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH3:15].[C:16]([O:20][C:21]([NH:23][C:24]1[CH:25]=[C:26]([CH:30]=[C:31]([C:33]([F:36])([F:35])[F:34])[CH:32]=1)[C:27]([OH:29])=O)=[O:22])([CH3:19])([CH3:18])[CH3:17]>CCCCCCC.CCOC(C)=O>[C:16]([O:20][C:21](=[O:22])[NH:23][C:24]1[CH:32]=[C:31]([C:33]([F:36])([F:35])[F:34])[CH:30]=[C:26]([C:27](=[O:29])[N:2]([CH3:1])[C:3]2[CH:4]=[N:5][CH:6]=[CH:7][C:8]=2[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH3:15])[CH:25]=1)([CH3:17])([CH3:18])[CH3:19]

Participants

4

Reactant 2

HCID 18403336N-methyl-4-o-tolylpyridin-3-amineHCID 612351163-(((Tert-butoxy)carbonyl)amino)-5-(trifluoromethyl)benzoic acid

Product 1

HCID 70663415{3-[Methyl-(4-o-tolyl-pyridin-3-yl)-carbamoyl]-5-trifluoromethyl-phenyl}-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 21899848Ethylacetate heptaneSolvent

Procedure

The title compound was prepared in analogy to example 90, from N-methyl-4-o-tolylpyridin-3-amine (example 1, intermediate a) and 3-tert-butoxycarbonylamino-5-trifluoromethyl-benzoic acid and using a gradient of n-heptane:EtOAc (100:0 to 0:60) for the chromatographic purification. Light brown solid (4%). MS (ESI): m/z=486.20 [M+H]+.

Workup

  1. customfor the chromatographic purification

Sources & evidence

ORD record
ord-c527e468dcf241f3947f06e777535315
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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