HCID 67265766, compound → N1-(2-Methoxy-4-methylbenzyl)-n2-(2-(5-methylpyridin-2-yl)ethyl)oxalamide

HRID 1686132Notes

Reaction equation

HRID 1686132 reaction equation
COC1C=C(C)C=CC=1C[N:6]([CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][N:15]=1)C(=O)C(N)=O.[CH3:26][O:27][C:28]1[CH:40]=[C:39]([CH3:41])[CH:38]=[CH:37][C:29]=1[CH2:30][NH:31][C:32](=[O:36])[C:33]([O-:35])=O>[Ni]>[CH3:26][O:27][C:28]1[CH:40]=[C:39]([CH3:41])[CH:38]=[CH:37][C:29]=1[CH2:30][NH:31][C:32](=[O:36])[C:33]([NH:6][CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][N:15]=1)=[O:35]

Participants

4

Reactant 2

HCID 67265766HCID 67265766, compoundHCID 866357512-(2-Methoxy-4-methylbenzylamino)-2-oxoacetate2×

Product 1

HCID 11210019N1-(2-Methoxy-4-methylbenzyl)-n2-(2-(5-methylpyridin-2-yl)ethyl)oxalamide

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

This method resulted in an improved yield of 85% when compared to the previous example (40%) yield by purification of compound 4 with column chromatography and by using H2/Raney Ni instead of BH3—SMe2. Further, the one-pot preparation of N′-(2-methoxy-4-methylbenzyl)-N2-(2-(5-methylpyridin-2-yl)ethyl) oxalamide shown in the previous example, was divided into two steps in this example. The yield was improved to 44% by purification of 2-(2-methoxy-4-methylbenzylamino)-2-oxoacetate in this example, from 30% yield without any purification of 2-(2-methoxy-4-methylbenzylamino)-2-oxoacetate in the one pot preparation described in the previous example.

Workup

  1. customThis method resulted in an improved yield of 85% when

Sources & evidence

ORD record
ord-c8e288fd88d548878f68f7c21cccb244
Source dataset
uspto-grants-2012_04
Patent number
US08148536B2

Reaction notes

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