Benzenemethanamine, 3,4-dichloro- → N2,3-bis(benzyloxy)-N5-(3,4-dichlorobenzyl)-4-(hydroxymethyl)pyridine-2,5-dicarboxamide

HRID 402568Notes

Reaction equation

HRID 402568 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[Cl:10])[CH2:5][NH2:6].[CH2:11]([O:18][NH:19][C:20]([C:22]1[C:27]([O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[C:26]([CH2:36][OH:37])[C:25]([C:38](NCC2C=CC(F)=CC=2)=[O:39])=[CH:24][N:23]=1)=[O:21])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>CN(C=O)C>[CH2:11]([O:18][NH:19][C:20]([C:22]1[C:27]([O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[C:26]([CH2:36][OH:37])[C:25]([C:38]([NH:6][CH2:5][C:4]2[CH:7]=[CH:8][C:9]([Cl:10])=[C:2]([Cl:1])[CH:3]=2)=[O:39])=[CH:24][N:23]=1)=[O:21])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 1608Benzenemethanamine, 3,4-dichloro-HCID 44540937N2,3-bis(benzyloxy)-N5-(4-fluorobenzyl)-4-(hydroxymethyl)pyridine-2,5-dicarboxamide2×

Product 1

HCID 44539697N2,3-bis(benzyloxy)-N5-(3,4-dichlorobenzyl)-4-(hydroxymethyl)pyridine-2,5-dicarboxamideYield 37.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3,4 diChloro benzylamine (0.060 g, 1.29 mmol, 2 eq) and N,7-bis(benzyloxy)-3-oxo-1,3-dihydrofuro[3,4-c]pyridine-6-carboxamide (0.050 g, 0.141 mmol, 1 eq) (compound 1c of example 1) were heated in DMF at 90° C. for 120 min. The crude product was purified by silica gel (100% ethyl acetate) yielding 0.03 g of N2,3-bis(benzyloxy)-N5-(3,4-dichlorobenzyl)-4-(hydroxymethyl)pyridine-2,5-dicarboxamide (29%) as a white solid; MS-ESI m/z 589 [MH]+.

Workup

  1. customThe crude product was purified by silica gel (100% ethyl acetate)

Sources & evidence

ORD record
ord-414b286eef8b49bb8035001fe43f4aa4
Source dataset
uspto-grants-2014_06
Patent number
US08742123B2

Reaction notes

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