N-(5-Iodo-4-methyl-2-thiazolyl)acetamide → N-{4-Methyl-5-[5-(2-morpholinoethylaminosulfonyl)pyridin-3-yl]-1,3-thiazol-2-yl}acetamide

HRID 252701Notes

Reaction equation

HRID 252701 reaction equation
I[C:2]1[S:6][C:5]([NH:7][C:8](=[O:10])[CH3:9])=[N:4][C:3]=1[CH3:11].Br[C:13]1[CH:14]=[C:15]([S:19]([NH:22][CH2:23][CH2:24][N:25]2[CH2:30][CH2:29][O:28][CH2:27][CH2:26]2)(=[O:21])=[O:20])[CH:16]=[N:17][CH:18]=1>>[CH3:11][C:3]1[N:4]=[C:5]([NH:7][C:8](=[O:10])[CH3:9])[S:6][C:2]=1[C:13]1[CH:18]=[N:17][CH:16]=[C:15]([S:19]([NH:22][CH2:23][CH2:24][N:25]2[CH2:30][CH2:29][O:28][CH2:27][CH2:26]2)(=[O:21])=[O:20])[CH:14]=1

Participants

3

Reactant 2

HCID 57417074N-(5-Iodo-4-methyl-2-thiazolyl)acetamideHCID 61795719HCID 61795719, compound

Product 1

HCID 86620381N-{4-Methyl-5-[5-(2-morpholinoethylaminosulfonyl)pyridin-3-yl]-1,3-thiazol-2-yl}acetamideYield 7%

Procedure

Using an analogous method to that described in Example 7, N-(5-iodo-4-methyl-1,3-thiazol-2-yl)acetamide was reacted with 5-bromo-N-(2-morpholinoethyl)pyridine-3-sulfonamide to give the title compound (Method A HPLC: retention time 3.7 minutes; 8 mg, 7%); 1H NMR Spectrum: (DMSOd6) 12.27 (1H, br s); 8.91 (1H, d); 8.87 (1H, d); 8.17 (1H, br t); 7.96 (1H, br s); 3.42 (4H, br t); 3.00 (2H, t); 2.40 (3H, s); 2.29 (2H, t); 2.22 (4H, br t); 2.16 (3H, s); Mass Spectrum: M+H+ 426.

Sources & evidence

ORD record
ord-96853c7955114723bebdf20c7c56b3a7
Source dataset
uspto-grants-2011_01
Patent number
US07868188B2

Reaction notes

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