2-(Methoxycarbonyl)-6-methylisonicotinic acid → Methyl 6-methyl-4-((1-(5-methyl-6-(2,2,2-trifluoroethoxy)pyridin-3-yl)ethyl)carbamoyl)picolinate

HRID 623645Notes

Reaction equation

HRID 623645 reaction equation
Cl.[CH3:2][C:3]1[CH:4]=[C:5]([CH:15]([NH2:17])[CH3:16])[CH:6]=[N:7][C:8]=1[O:9][CH2:10][C:11]([F:14])([F:13])[F:12].[CH3:18][O:19][C:20]([C:22]1[CH:23]=[C:24]([CH:28]=[C:29]([CH3:31])[N:30]=1)[C:25](O)=[O:26])=[O:21]>>[CH3:31][C:29]1[N:30]=[C:22]([C:20]([O:19][CH3:18])=[O:21])[CH:23]=[C:24]([C:25](=[O:26])[NH:17][CH:15]([C:5]2[CH:6]=[N:7][C:8]([O:9][CH2:10][C:11]([F:14])([F:12])[F:13])=[C:3]([CH3:2])[CH:4]=2)[CH3:16])[CH:28]=1

Participants

3

Reactant 2

HCID 595708792-(Methoxycarbonyl)-6-methylisonicotinic acidHCID 675095881-(5-Methyl-6-(2,2,2-trifluoroethoxy)pyridin-3-yl)ethanamine hydrochloride

Product 1

HCID 67509260Methyl 6-methyl-4-((1-(5-methyl-6-(2,2,2-trifluoroethoxy)pyridin-3-yl)ethyl)carbamoyl)picolinateYield 72%

Procedure

The title compound is prepared in 72% yield (110 mg, clear colorless oil) from 1-(5-methyl-6-(2,2,2-trifluoroethoxy)pyridin-3-yl)ethanamine hydrochloride (97 mg, 0.36 mmol, Amine-17, single enantiomer) and 2-(methoxycarbonyl)-6-methylisonicotinic acid (70 mg, 0.36 mmol) by the similar manner in Step-1 of Example 8.

Sources & evidence

ORD record
ord-d636837a02994572a1794964fe6f2468
Source dataset
uspto-grants-2016_04
Patent number
US09302991B2

Reaction notes

Loading…