Benzo-1,3-dioxole-5-methylamine → N5-(1,3-benzodioxol-5-ylmethyl)-N2,3-dibenzyloxy-4-(hydroxymethyl)pyridine-2,5-dicarboxamide

HRID 402559Notes

Reaction equation

HRID 402559 reaction equation
[CH2:1]([NH2:11])[C:2]1[CH:10]=[CH:9][C:8]2[O:7][CH2:6][O:5][C:4]=2[CH:3]=1.[CH2:12]([O:19][NH:20][C:21]([C:23]1[N:28]=[CH:27][C:26]2[C:29](=[O:32])[O:30][CH2:31][C:25]=2[C:24]=1[O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:22])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(ONC(C1C(OCC2C=CC=CC=2)=C(CO)C(C(NCC2C=CC(F)=CC=2)=O)=CN=1)=O)C1C=CC=CC=1>>[O:7]1[C:8]2[CH:9]=[CH:10][C:2]([CH2:1][NH:11][C:29]([C:26]3[C:25]([CH2:31][OH:30])=[C:24]([O:33][CH2:34][C:35]4[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=4)[C:23]([C:21]([NH:20][O:19][CH2:12][C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=4)=[O:22])=[N:28][CH:27]=3)=[O:32])=[CH:3][C:4]=2[O:5][CH2:6]1

Participants

4

Reactant 3

HCID 75799Benzo-1,3-dioxole-5-methylamineHCID 44540937N2,3-bis(benzyloxy)-N5-(4-fluorobenzyl)-4-(hydroxymethyl)pyridine-2,5-dicarboxamideHCID 86655922N,7-bis(benzyloxy)-3-oxo-1,3-dihydrofuro[3,4-c]pyridine-6-carboxamide

Product 1

HCID 71589574N5-(1,3-benzodioxol-5-ylmethyl)-N2,3-dibenzyloxy-4-(hydroxymethyl)pyridine-2,5-dicarboxamideYield 62%

Procedure

Piperonylamine (0.035 g, 0.288 mmol, 2 eq) and N,7-bis(benzyloxy)-3-oxo-1,3-dihydrofuro[3,4-c]pyridine-6-carboxamide (0.056 g, 0.144 mmol, 1 eq), compound 1c of example 1, were heated neat at 70° C. for 30 min. The crude product was purified by silica gel (30% ethyl acetate) yielding 0.048 g of N5-(benzo[d][1,3]dioxol-5-ylmethyl)-N2,3-bis(benzyloxy)-4-(hydroxymethyl)pyridine-2,5-dicarboxamide (62% yield) as a white solid; MS-ESI m/z 542 [MH]+.

Workup

  1. customThe crude product was purified by silica gel (30% ethyl acetate)

Sources & evidence

ORD record
ord-f0ad9ab260ea449f84fabff119eed731
Source dataset
uspto-grants-2014_06
Patent number
US08742123B2

Reaction notes

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