3-Chloro-4-fluorobenzylamine → N2,3-bis(benzyloxy)-N5-(3-chloro-4-fluorobenzyl)-4-(hydroxymethyl)pyridine-2,5-dicarboxamide

HRID 402566Notes

Reaction equation

HRID 402566 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH2:7])=[CH:4][C:3]=1[Cl:10].[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:7][CH2:6][C:5]2[CH:8]=[CH:9][C:2]([F:1])=[C:3]([Cl:10])[CH:4]=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 1445393-Chloro-4-fluorobenzylamineHCID 44540937N2,3-bis(benzyloxy)-N5-(4-fluorobenzyl)-4-(hydroxymethyl)pyridine-2,5-dicarboxamide2×

Product 1

HCID 44541112N2,3-bis(benzyloxy)-N5-(3-chloro-4-fluorobenzyl)-4-(hydroxymethyl)pyridine-2,5-dicarboxamideYield 38.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Fluoro-3-Chloro 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-chloro-4-fluorobenzyl)-4-(hydroxymethyl)pyridine-2,5-dicarboxamide as a white solid; MS-ESI m/z 573 [MH]−.

Workup

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

Sources & evidence

ORD record
ord-38d9f56761ae479a83b93bb9c65a0bff
Source dataset
uspto-grants-2014_06
Patent number
US08742123B2

Reaction notes

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