5-Chloro-2-picolinic acid → HCID 66624419, compound

HRID 416507Notes

Reaction equation

HRID 416507 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([OH:10])=O)=[N:6][CH:7]=1.[CH:11]([N:14]1[CH2:19][CH2:18][CH:17]([NH:20][S:21]([CH2:24][CH2:25][NH2:26])(=[O:23])=[O:22])[CH2:16][CH2:15]1)([CH3:13])[CH3:12]>>[CH:11]([N:14]1[CH2:19][CH2:18][CH:17]([NH:20][S:21]([CH2:24][CH2:25][NH:26][C:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][N:6]=2)=[O:10])(=[O:22])=[O:23])[CH2:16][CH2:15]1)([CH3:13])[CH3:12].[CH:11]([N:14]1[CH2:15][CH2:16][CH:17]([S+:21]=[CH:24][CH2:25][NH:26][C:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][N:6]=2)=[O:10])[CH2:18][CH2:19]1)([CH3:12])[CH3:13]

Participants

4

Reactant 2

HCID 27628725-Chloro-2-picolinic acidHCID 666246312-Amino-ethanesulfonic acid (1-isopropyl-piperidin-4-yl)-amide

Product 2

HCID 66624419HCID 66624419, compoundHCID 178456312HCID 178456312, compound

Procedure

5-Chloro-pyridine-2-carboxylic acid[2-(1-isopropyl-piperidin-4-ylsulfamoyl)-ethyl]-amide was prepared by an analogous procedure as described in example 9 starting from 104 mg (1.1 equiv.) 5-chloro-pyridine-2-carboxylic acid and 150 mg (0.60 mmol) 2-amino-ethanesulfonic acid (1-isopropyl-piperidin-4-yl)-amide. Final purification by preparative RP-HPLC (CH3CN/H2O gradient+0.1% TFA) gave pure 5-chloro-pyridine-2-carboxylic acid [2-(1-isopropyl-piperidin-4-ylsulfamo-yl)-ethyl]-amide. The title compound was obtained as its trifluoroacetate in form of a colorless amorphous material. Yield: 60 mg MS (ES+): m/e=389, chloro pattern.

Workup

  1. customFinal purification by preparative RP-HPLC (CH3CN/H2O gradient+0.1% TFA)

Sources & evidence

ORD record
ord-0d760bd3486b42fa9367fb3b30b00b1f
Source dataset
uspto-grants-2012_01
Patent number
US08088925B2

Reaction notes

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