3-(Chloromethyl)pyridine hydrochloride → HCID 66624915, compound

HRID 416515Notes

Reaction equation

HRID 416515 reaction equation
Cl.Cl[CH2:3][C:4]1[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=1.[CH:10]([N:13]1[CH2:18][CH2:17][CH:16]([NH:19][S:20]([CH2:23][CH2:24][NH:25][C:26]([C:28]2[S:29][C:30]([Cl:33])=[CH:31][CH:32]=2)=[O:27])(=[O:22])=[O:21])[CH2:15][CH2:14]1)([CH3:12])[CH3:11]>>[CH:10]([N:13]1[CH2:18][CH2:17][CH:16]([N:19]([CH2:3][C:4]2[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=2)[S:20]([CH2:23][CH2:24][NH:25][C:26]([C:28]2[S:29][C:30]([Cl:33])=[CH:31][CH:32]=2)=[O:27])(=[O:21])=[O:22])[CH2:15][CH2:14]1)([CH3:12])[CH3:11]

Participants

3

Reactant 2

HCID 233943-(Chloromethyl)pyridine hydrochlorideHCID 119904785-Chloro-Thiophene-2-Carboxylic Acid [2-(1--Isopropyl-Piperidin-4-Ylsulfamoyl)-Ethyl]-Amide

Product 1

HCID 66624915HCID 66624915, compound

Procedure

5-Chloro-thiophene-2-carboxylic acid {2-[(1-isopropyl-piperidin-4-yl)-pyridin-3-ylmethyl-sulfamoyl]-ethyl}-amide was prepared by an analogous procedure as described in example 15 starting from 83 mg (1 equiv.) 3-chloromethyl-pyridine hydrochloride and 200 mg (0.50 mmol) 5-chloro-thiophene-2-carboxylic acid [2-(1-isopropyl-piperidin-4-ylsulfamoyl)-ethyl]-amide (reaction temperature: 60° C.). Final purification by preparative RP-HPLC (CH3CN/H2O gradient+0.1% TFA) gave pure 5-chloro-thiophene-2-carboxylic acid {2-[(1-isopropyl-piperidin-4-yl)-pyridin-3-ylmethyl-sulfamoyl]-ethyl}-amide. The title compound was obtained as its trifluoroacetate in form of a light yellow amorphous material.

Workup

  1. custom5-Chloro-thiophene-2-carboxylic acid {2-[(1-isopropyl-piperidin-4-yl)-pyridin-3-ylmethyl-sulfamoyl]-ethyl}-amide was prepared by an analogous procedure
  2. customFinal purification by preparative RP-HPLC (CH3CN/H2O gradient+0.1% TFA)

Sources & evidence

ORD record
ord-32d3a89800184ce2bdd9468c4bd1f00b
Source dataset
uspto-grants-2012_01
Patent number
US08088925B2

Reaction notes

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