6-chloro-N-(cyclopropylmethyl)pyridine-3-carboxamide → N-Cyclopropyhnethyl-6-[5-(thiadiazol-2-ylcarbamoyl)-2-methyl-phenyl]-nicotinamide

HRID 2037255Notes

Reaction equation

HRID 2037255 reaction equation
Cl[C:2]1[CH:14]=[CH:13][C:5]([C:6]([NH:8][CH2:9][CH:10]2[CH2:12][CH2:11]2)=[O:7])=[CH:4][N:3]=1.[CH3:15][C:16]1[CH:29]=[CH:28][C:19]([C:20]([NH:22][N:23]2[NH:27][CH:26]=[CH:25][S:24]2)=[O:21])=[CH:18][C:17]=1B1OC(C)(C)C(C)(C)O1>>[CH:10]1([CH2:9][NH:8][C:6](=[O:7])[C:5]2[CH:13]=[CH:14][C:2]([C:17]3[CH:18]=[C:19]([C:20](=[O:21])[NH:22][N:23]4[NH:27][CH:26]=[CH:25][S:24]4)[CH:28]=[CH:29][C:16]=3[CH3:15])=[N:3][CH:4]=2)[CH2:12][CH2:11]1

Participants

3

Reactant 2

HCID 112758456-chloro-N-(cyclopropylmethyl)pyridine-3-carboxamide2×HCID 219146524-Methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-N-(thiadiazol-2-yl)-benzamide2×

Product 1

HCID 21914632N-Cyclopropyhnethyl-6-[5-(thiadiazol-2-ylcarbamoyl)-2-methyl-phenyl]-nicotinamide

Procedure

N-Cyclopropylmethyl-6-[5-(thiadiazol-2-ylcarbamoyl)-2-methyl-phenyl]-nicotinamide was prepared from 6-chloro-N-cyclopropylmethylnicotinamide (Intermediate 1) 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 2.79 min, MH− 394. NMR: δH [2H6]-DMSO 13.14, (1H, b), 9.24, (1H, s), 9.14, (1H, s), 8.86, (1H, t), 8.35, (1H, d), 8.25, (1H, s), 8.10, (1H, d), 7.82, (1H, d), 7.54, (1H, d), 3.21, (2H, t), 2.46, (3H, s), 1.07, (1H, m), 0.47, (2H, m), 0.27, (2H, m).

Sources & evidence

ORD record
ord-01c10a9fbc4540d4a325c978c7fba28b
Source dataset
uspto-grants-2013_11
Patent number
US08575204B2

Reaction notes

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