6-chloro-N-(3-methylsulphonylaminobenzyl)nicotinamide → 6-(5-Cyclopropylcarbamoyl-2-methyl-phenyl)-N-(3-methylsulphonylaminobenzyl)-nicotinamide

HRID 1246044Notes

Reaction equation

HRID 1246044 reaction equation
Cl[C:2]1[CH:22]=[CH:21][C:5]([C:6]([NH:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([NH:16][S:17]([CH3:20])(=[O:19])=[O:18])[CH:11]=2)=[O:7])=[CH:4][N:3]=1.[CH:23]1([NH:26][C:27](=[O:44])[C:28]2[CH:33]=[CH:32][C:31]([CH3:34])=[C:30](B3OC(C)(C)C(C)(C)O3)[CH:29]=2)[CH2:25][CH2:24]1>>[CH:23]1([NH:26][C:27]([C:28]2[CH:33]=[CH:32][C:31]([CH3:34])=[C:30]([C:2]3[CH:22]=[CH:21][C:5]([C:6]([NH:8][CH2:9][C:10]4[CH:15]=[CH:14][CH:13]=[C:12]([NH:16][S:17]([CH3:20])(=[O:19])=[O:18])[CH:11]=4)=[O:7])=[CH:4][N:3]=3)[CH:29]=2)=[O:44])[CH2:24][CH2:25]1

Participants

3

Reactant 2

HCID 219145456-chloro-N-(3-methylsulphonylaminobenzyl)nicotinamide2×HCID 21914577N-cyclopropyl-4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide2×

Product 1

HCID 219145366-(5-Cyclopropylcarbamoyl-2-methyl-phenyl)-N-(3-methylsulphonylaminobenzyl)-nicotinamide

Procedure

6-(5-Cyclopropylcarbamoyl-2-methyl-phenyl)-N-(3-methylsulphonylaminobenzyl)-nicotinamide was prepared from 6-chloro-N-(3-methylsulphonylaminobenzyl)nicotinamide (Intermediate 4) and N-cyclopropyl-4-methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzamide (Intermediate 8) using General Method B. LCMS: retention time 2.71 min, MH+ 479. NMR: δH [2H6]-DMSO 9.33,(1H, t), 9.15,(1H, s), 8.48–8.33,(3H, m), 7.89,(1H, s), 7.81,(1H, d), 7.73,(1H, d), 7.41,(1H, d), 7.31,(1H, t), 7.21,(1H, s), 7.10,(2H, m), 4.51,(2H, d), 2.99,(3H, s), 2.86,(1H, m), 2.38,(3H, s), 0.69,(2H, m), 0.57,(2H, m).

Sources & evidence

ORD record
ord-a887a91a7bd7401d88b1127b4f2bb305
Source dataset
uspto-grants-2006_10
Patent number
US07125898B2

Reaction notes

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