6-chloro-N-[2-(4-methylpiperazin-1-ylmethyl)phenyl]nicotinamide → N-[2-(4-Methylpiperazin-1-ylmethyl)phenyl]-6-[2-methyl-5-(thiadiazol-2-ylcarbamoyl)-phenyl]-nicotinamide

HRID 2037278Notes

Reaction equation

HRID 2037278 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.[CH3:25][C:26]1[CH:39]=[CH:38][C:29]([C:30]([NH:32][N:33]2[NH:37][CH:36]=[CH:35][S:34]2)=[O:31])=[CH:28][C:27]=1B1OC(C)(C)C(C)(C)O1>>[CH3:22][N:19]1[CH2:20][CH2:21][N:16]([CH2:15][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[NH:8][C:6](=[O:7])[C:5]2[CH:23]=[CH:24][C:2]([C:27]3[CH:28]=[C:29]([C:30](=[O:31])[NH:32][N:33]4[NH:37][CH:36]=[CH:35][S:34]4)[CH:38]=[CH:39][C:26]=3[CH3:25])=[N:3][CH:4]=2)[CH2:17][CH2:18]1

Participants

3

Reactant 2

HCID 219145746-chloro-N-[2-(4-methylpiperazin-1-ylmethyl)phenyl]nicotinamide2×HCID 219146524-Methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-N-(thiadiazol-2-yl)-benzamide2×

Product 1

HCID 21914610N-[2-(4-Methylpiperazin-1-ylmethyl)phenyl]-6-[2-methyl-5-(thiadiazol-2-ylcarbamoyl)-phenyl]-nicotinamide

Procedure

N-[2-(4-Methylpiperazin-1-ylmethyl)phenyl]-6-[2-methyl-5-(thiadiazol-2-ylcarbamoyl)-phenyl]-nicotinamide was prepared from 6-chloro-N-[2-(4-methylpiperazin-1-ylmethyl)phenyl]nicotinamide (Intermediate 5) and 4-methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-N-(thiadiazol-2-yl)-benzamide (Intermediate 12) using General Method B. LCMS: retention time 2.43 min, MH+ 528. NMR: δH [2H6]-DMSO 13.07, (1H, b), 11.74, (1H, s), 9.26, (1H, s), 9.21, (1H, s), 8.43, (1H, d), 8.34, (1H, d), 8.29, (1H, s), 8.12, (1H, d), 7.93, (1H, d), 7.56, (1H, d), 7.36, (1H, t), 7.29, (1H, d), 7.11, (1H, t), 3.78, (2H, s), 2.67-2.26, (11H, m), 2.11, (3H, s).

Sources & evidence

ORD record
ord-4e8155a6d6d548dbb25c911f698183b1
Source dataset
uspto-grants-2013_11
Patent number
US08575204B2

Reaction notes

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