Thionyl Chloride → 5-Bromo-N-{(2R)-3-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-2-hydroxypropyl}-6-oxo-2-(trifluoromethyl)-1,6-dihydropyridine-3-carboxamide

HRID 2421015Notes

Reaction equation

HRID 2421015 reaction equation
[Br:1][C:2]1[C:7](=[O:8])[NH:6][C:5]([C:9]([F:12])([F:11])[F:10])=[C:4]([C:13]([OH:15])=O)[CH:3]=1.S(Cl)(Cl)=O.[NH2:20][CH2:21][C@@H:22]([OH:39])[CH2:23][N:24]1[CH2:29][CH2:28][CH:27]([O:30][C:31]2[CH:36]=[CH:35][C:34]([Cl:37])=[C:33]([Cl:38])[CH:32]=2)[CH2:26][CH2:25]1>C(N(CC)CC)C>[Br:1][C:2]1[C:7](=[O:8])[NH:6][C:5]([C:9]([F:10])([F:11])[F:12])=[C:4]([C:13]([NH:20][CH2:21][C@@H:22]([OH:39])[CH2:23][N:24]2[CH2:29][CH2:28][CH:27]([O:30][C:31]3[CH:36]=[CH:35][C:34]([Cl:37])=[C:33]([Cl:38])[CH:32]=3)[CH2:26][CH2:25]2)=[O:15])[CH:3]=1

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 11151315(2R)-1-amino-3-[4-(3,4-dichlorophenoxy)piperidin-1-yl)propan-2-olHCID 672150065-Bromo-6-oxo-2-(trifluoromethyl)-1,6-dihydropyridine-3-carboxylic acid

Product 1

HCID 117866225-Bromo-N-{(2R)-3-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-2-hydroxypropyl}-6-oxo-2-(trifluoromethyl)-1,6-dihydropyridine-3-carboxamideYield 46.8%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Made by the method of Example 1 using 5-bromo-6-oxo-2-(trifluoromethyl)-1,6-dihydropyridine-3-carboxylic acid (0.10 g), thionyl chloride (2 mL), (2R)-1-amino-3-[4-(3,4-dichlorophenoxy)piperidin-1-yl]propan-2-ol (0.112 g) and triethylamine (0.244 mL) to yield the title compound as a colourless solid (0.096 g).

Sources & evidence

ORD record
ord-fe3d3f8b64d94024a3cfca68eb821ca7
Source dataset
uspto-grants-2011_06
Patent number
US07956070B2

Reaction notes

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