3,5-Difluorobenzylamine → N2,3-bis(benzyloxy)-N5-(3,5-difluorobenzyl)-4-(hydroxymethyl)pyridine-2,5-dicarboxamide

HRID 402562Notes

Reaction equation

HRID 402562 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([F:10])[CH:9]=1)[CH2:5][NH2:6].[CH2:11]([O:18][NH:19][C:20]([C:22]1[N:27]=[CH:26][C:25]2[C:28](=[O:31])[O:29][CH2:30][C:24]=2[C:23]=1[O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:21])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>>[CH2:11]([O:18][NH:19][C:20]([C:22]1[C:23]([O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[C:24]([CH2:30][OH:29])[C:25]([C:28]([NH:6][CH2:5][C:4]2[CH:3]=[C:2]([F:1])[CH:9]=[C:8]([F:10])[CH:7]=2)=[O:31])=[CH:26][N:27]=1)=[O:21])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

3

Reactant 2

HCID 1452113,5-DifluorobenzylamineHCID 86655922N,7-bis(benzyloxy)-3-oxo-1,3-dihydrofuro[3,4-c]pyridine-6-carboxamide

Product 1

HCID 44541026N2,3-bis(benzyloxy)-N5-(3,5-difluorobenzyl)-4-(hydroxymethyl)pyridine-2,5-dicarboxamideYield 26.8%

Procedure

3,5-difluorobenzylamine (0.02 g, 0.154 mmol, 2.5 eq) and N,7-bis(benzyloxy)-3-oxo-1,3-dihydrofuro[3,4-c]pyridine-6-carboxamide (0.030 g, 0.077 mmol, 1 eq) were heated neat at 70° C. for 30 min. The crude product was purified by silica gel (100% ethyl acetate) yielding 0.011 g of N2,3-bis(benzyloxy)-N5-(3,5-difluorobenzyl)-4-(hydroxymethyl)pyridine-2,5-dicarboxamide (15% yield) as a white solid; MS-ESI m/z 534 [MH]+.

Workup

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

Sources & evidence

ORD record
ord-77634780ab11404399d75b45a3933169
Source dataset
uspto-grants-2014_06
Patent number
US08742123B2

Reaction notes

Loading…