5-Chloro-2-picolinic acid → 5-Chloro-pyridine-2-carboxylic acid (3-[1,3]dioxolan-2-yl-phenyl)-amide

HRID 1486746Notes

Reaction equation

HRID 1486746 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([OH:10])=O)=[N:6][CH:7]=1.[CH2:11]1[O:22][CH:14]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([NH2:21])[CH:16]=2)[O:13][CH2:12]1>>[O:13]1[CH2:12][CH2:11][O:22][CH:14]1[C:15]1[CH:16]=[C:17]([NH:21][C:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][N:6]=2)=[O:10])[CH:18]=[CH:19][CH:20]=1

Participants

3

Reactant 2

HCID 27628725-Chloro-2-picolinic acidHCID 70203623-(1,3-Dioxolan-2-yl)aniline

Product 1

HCID 1317368165-Chloro-pyridine-2-carboxylic acid (3-[1,3]dioxolan-2-yl-phenyl)-amide

Procedure

The title compound is prepared according to the reaction sequence described above for L-7 starting from 5-chloropyridine-2-carboxylic acid and 3-aminobenzaldehyde ethylene acetal to yield 5-chloro-pyridine-2-carboxylic acid (3-[1,3]dioxolan-2-yl-phenyl)-amide; LC-MS A: tR=0.84 min; [M+H]+=305.13 which is treated with m-chloro-perbenzoic acid to deliver 5-chloro-1-oxy-pyridine-2-carboxylic acid (3-[1,3]dioxolan-2-yl-phenyl)-amide; LC-MS A: tR=0.77 min; [M+H]+=321.02, then deprotected with HCl 10% to yield 5-chloro-1-oxy-pyridine-2-carboxylic acid (3-formyl-phenyl)-amide LC-MS A: tR=0.72 min; [M+H]+=277.01.

Sources & evidence

ORD record
ord-6209ae4940e14b66b6225e6a60208ccf
Source dataset
uspto-grants-2016_08
Patent number
US09428456B2

Reaction notes

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