6-chloro-N-[2-(4-methylpiperazin-1-ylmethyl)phenyl]nicotinamide → HCID 21914645, compound

HRID 2108992Notes

Reaction equation

HRID 2108992 reaction equation
Cl[C:2]1[CH:24]=[CH:23][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH2:15][N:16]2[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][CH2:17]2)=[O:7])=[CH:4][N:3]=1.[CH:25]1([CH2:28][NH:29][C:30](=[O:47])[C:31]2[CH:36]=[CH:35][C:34]([CH3:37])=[C:33](B3OC(C)(C)C(C)(C)O3)[CH:32]=2)[CH2:27][CH2:26]1>>[CH:25]1([CH2:28][NH:29][C:30]([C:31]2[CH:32]=[CH:33][C:34]([CH3:37])=[C:35]([C:2]3[CH:24]=[CH:23][C:5]([C:6]([NH:8][C:9]4[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=4[CH2:15][N:16]4[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][CH2:17]4)=[O:7])=[CH:4][N:3]=3)[CH:36]=2)=[O:47])[CH2:27][CH2:26]1

Participants

3

Reactant 2

HCID 219145746-chloro-N-[2-(4-methylpiperazin-1-ylmethyl)phenyl]nicotinamide2×HCID 21914588N-cyclopropylmethyl-4-methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzamide2×

Product 1

HCID 21914645HCID 21914645, compound

Procedure

6-(5-Cyclopropylmethylcarbamoyl-2-methyl-phenyl)-N-[2-(4-methylpiperazin-1-ylmethyl)phenyl]-nicotinamide was prepared from 6-chloro-N-[2-(4-methylpiperazin-1-ylmethyl)phenyl]nicotinamide (Intermediate 5) and N-cyclopropylmethyl-4-methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzamide (Intermediate 10) using General Method B. LCMS: retention time 2.46 min, MH+498. NMR: δH [2H6]-DMSO 11.67, (1H, b), 9.24, (1H, s), 8.63, (1H, t), 8.39, (1H, d), 8.32, (1H, d), 7.97, (1H, s), 7.88-7.83, (2H, m), 7.45, (1H, d), 7.36, (1H, t), 7.30, (1H, d), 7.11, (1H, t), 3.77, (2H, s), 3.15, (2H, t), 2.70-2.21, (11H, m), 1.04, (1H, m), 0.43, (2H, m), 0.23, (2H, m).

Sources & evidence

ORD record
ord-d8323e3e9ec341b2b20b6b55a219c1e2
Source dataset
uspto-grants-2009_04
Patent number
US07514456B2

Reaction notes

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