6-chloro-N-(3-methoxybenzyl)nicotinamide → 6-[5-(Fur-3-ylcarbonylamino)-2-methyl-phenyl]-N-(3-methoxybenzyl)nicotinamide

HRID 2037269Notes

Reaction equation

HRID 2037269 reaction equation
Cl[C:2]1[CH:19]=[CH:18][C:5]([C:6]([NH:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH3:17])[CH:11]=2)=[O:7])=[CH:4][N:3]=1.[CH3:20][C:21]1[CH:26]=[CH:25][C:24]([NH:27][C:28]([C:30]2[CH:34]=[CH:33][O:32][CH:31]=2)=[O:29])=[CH:23][C:22]=1B1OC(C)(C)C(C)(C)O1>>[O:32]1[CH:33]=[CH:34][C:30]([C:28]([NH:27][C:24]2[CH:23]=[CH:22][C:21]([CH3:20])=[C:26]([C:2]3[CH:19]=[CH:18][C:5]([C:6]([NH:8][CH2:9][C:10]4[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH3:17])[CH:11]=4)=[O:7])=[CH:4][N:3]=3)[CH:25]=2)=[O:29])=[CH:31]1

Participants

3

Reactant 2

HCID 94957946-chloro-N-(3-methoxybenzyl)nicotinamide2×HCID 21914573N-[4-Methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-3-furamide2×

Product 1

HCID 219146476-[5-(Fur-3-ylcarbonylamino)-2-methyl-phenyl]-N-(3-methoxybenzyl)nicotinamide

Procedure

6-[5-(Fur-3-ylcarbonylamino)-2-methyl-phenyl]-N-(3-methoxybenzyl)-nicotinamide was prepared from 6-chloro-N-(3-methoxybenzyl)nicotinamide (Intermediate 3) and N-[4-methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-3-furamide (Intermediate 13) using General Method B. LCMS: retention time 3.17 min, MH 442. NMR: δH [2H6]-DMSO 9.99, (1H, s), 9.29, (1H, t), 9.15, (1H, d), 8.38, (1H, s), 8.34, (1H, dd), 7.81, (2H, m), 7.75, (1H, d), 7.67, (1H, d), 7.31-7.25, (2H, m), 7.00 (1H, s), 6.94, (2H, m), 6.84, (1H, d), 4.51, (2H, d), 3.75, (3H, s), 2.32, (3H, s).

Sources & evidence

ORD record
ord-24f7fee46c4f43c093191b9ef78153be
Source dataset
uspto-grants-2013_11
Patent number
US08575204B2

Reaction notes

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