2,6-Lutidine → N-(6-amino-5-iodopyridine-2-yl)-1-isopropyl-1H-pyrazole-5-carboxamide

HRID 1094814Notes

Reaction equation

HRID 1094814 reaction equation
[I:1][C:2]1[C:3]([NH2:9])=[N:4][C:5]([NH2:8])=[CH:6][CH:7]=1.N1C(C)=CC=CC=1C.[CH:18]([N:21]1[C:25]([C:26](O)=[O:27])=[CH:24][CH:23]=[N:22]1)([CH3:20])[CH3:19]>>[NH2:9][C:3]1[N:4]=[C:5]([NH:8][C:26]([C:25]2[N:21]([CH:18]([CH3:20])[CH3:19])[N:22]=[CH:23][CH:24]=2)=[O:27])[CH:6]=[CH:7][C:2]=1[I:1]

Participants

4

Reactant 3

HCID 79372,6-LutidineHCID 4762183-Iodopyridine-2,6-diamineHCID 31509471-(propan-2-yl)-1H-pyrazole-5-carboxylic acid

Product 1

HCID 66637081N-(6-amino-5-iodopyridine-2-yl)-1-isopropyl-1H-pyrazole-5-carboxamideYield 38%

Procedure

Method A using 3-Iodo-pyridine-2,6-diamine (Preparation 44), 1.6 equivalents of lutidine and 1.5 equivalents of acid chloride prepared from 2-isopropyl-2H-pyrazole-3-carboxylic acid. Purified by trituration with methanol:ethylacetate 1:2 to afford the title compound as a colourless oil (608 mg, 38%).

Workup

  1. customPurified by trituration with methanol:ethylacetate 1:2

Sources & evidence

ORD record
ord-996c29b2e0a44cb49fb77217aae9ecf3
Source dataset
uspto-grants-2012_03
Patent number
US08134007B2

Reaction notes

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