Cyclohexylamine → 5-(Aminomethyl)-pyridine-2-carboxylic acid cyclohexylamide

HRID 911297Notes

Reaction equation

HRID 911297 reaction equation
[CH:1]1([NH2:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(OC([NH:15][CH2:16][C:17]1[CH:18]=[CH:19][C:20]([C:23]([O-])=[O:24])=[N:21][CH:22]=1)=O)(C)(C)C.[Li+].CCN(C(C)C)C(C)C>>[CH:1]1([NH:7][C:23]([C:20]2[CH:19]=[CH:18][C:17]([CH2:16][NH2:15])=[CH:22][N:21]=2)=[O:24])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 7965CyclohexylamineHCID 81531DiisopropylethylamineHCID 57656023Lithium 5-(tert-butoxycarbonylamino-methyl)-pyridine-2-carboxylate

Product 1

HCID 576562475-(Aminomethyl)-pyridine-2-carboxylic acid cyclohexylamideYield 22%

Procedure

Use the General Procedure 6-2, using cyclohexylamine (1 mL), lithium 5-(tert-butoxycarbonylamino-methyl)-pyridine-2-carboxylate (1 g, 3.96 mmol) and DIEA (5 mL) as cosolvent, to give the title compound as a white solid (200 mg, 22%). MS (ES+) m/z: 234 (M+H)+.

Sources & evidence

ORD record
ord-04514008ab6f43af82bea344eb42fd9c
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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