4-(Hydroxymethyl)benzeneboronic acid → 1-(Benzo[d][1,3]dioxol-5-yl)-N-(5-(4-(hydroxymethyl)phenyl)-6-methylpyridin-3-yl)cyclopropanecarboxamide

HRID 2401928Notes

Reaction equation

HRID 2401928 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1.[O:12]1[C:16]2[CH:17]=[CH:18][C:19]([C:21]3([C:24]([NH:26][C:27]4[CH:28]=[N:29][C:30]([CH3:34])=[C:31](Br)[CH:32]=4)=[O:25])[CH2:23][CH2:22]3)=[CH:20][C:15]=2[O:14][CH2:13]1.O1C2C=CC(C3(C(NC4C=NC(C)=C(C5C=CC=CC=5)C=4)=O)CC3)=CC=2OC1>>[O:12]1[C:16]2[CH:17]=[CH:18][C:19]([C:21]3([C:24]([NH:26][C:27]4[CH:28]=[N:29][C:30]([CH3:34])=[C:31]([C:6]5[CH:7]=[CH:8][C:3]([CH2:2][OH:1])=[CH:4][CH:5]=5)[CH:32]=4)=[O:25])[CH2:23][CH2:22]3)=[CH:20][C:15]=2[O:14][CH2:13]1

Participants

4

Reactant 3

HCID 27347064-(Hydroxymethyl)benzeneboronic acidHCID 442061041-(benzo[d][1,3]dioxol-5-yl)-N-(5-bromo-6-methylpyridin-3-yl)cyclopropanecarboxamideHCID 442063231-(benzo[d][1,3]dioxol-5-yl)-N-(6-methyl-5-phenylpyridin-3-yl)cyclopropanecarboxamide

Product 1

HCID 578561881-(Benzo[d][1,3]dioxol-5-yl)-N-(5-(4-(hydroxymethyl)phenyl)-6-methylpyridin-3-yl)cyclopropanecarboxamide

Procedure

1-(Benzo[d][1,3]dioxol-5-yl)-N-(5-(4-(hydroxymethyl)phenyl)-6-methylpyridin-3-yl)cyclopropanecarboxamide was prepared from 4-(hydroxymethyl)phenylboronic acid and 1-(benzo[d][1,3]dioxol-5-yl)-N-(5-bromo-6-methylpyridin-3-yl)cyclopropanecarboxamide in a manner analogous to that of 1-(benzo[d][1,3]dioxol-5-yl)-N-(6-methyl-5-phenylpyridin-3-yl)cyclopropanecarboxamide.

Sources & evidence

ORD record
ord-70ea69428b8444cb86cca74b6ba575ad
Source dataset
uspto-grants-2014_08
Patent number
US08796312B2

Reaction notes

Loading…