3-Amino-5-bromo-2-chloropyridine → N-[5-(5-amino-6-chloropyridin-3-yl)-4-methyl-1,3-thiazol-2-yl]acetamide

HRID 252703Notes

Reaction equation

HRID 252703 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]([NH2:20])[C:16]([Cl:19])=[N:17][CH:18]=1>>[NH2:20][C:15]1[CH:14]=[C:13]([C:2]2[S:6][C:5]([NH:7][C:8](=[O:10])[CH3:9])=[N:4][C:3]=2[CH3:11])[CH:18]=[N:17][C:16]=1[Cl:19]

Participants

3

Reactant 2

HCID 218583543-Amino-5-bromo-2-chloropyridineHCID 57417074N-(5-Iodo-4-methyl-2-thiazolyl)acetamide

Product 1

HCID 86244450N-[5-(5-amino-6-chloropyridin-3-yl)-4-methyl-1,3-thiazol-2-yl]acetamideYield 25%

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-2-chloropyridin-3-amine to give the title compound (Method A HPLC: retention time 5.5 minutes) in 25% yield; 1H NMR Spectrum: (acetone-d6) 12.17 (1H, br s); 7.68 (1H, d); 7.20 (1H, d); 5.70 (2H, br s); 2.34 (3H, s); 2.14 (3H, s); Mass Spectrum: M+H+ 283 and 285.

Sources & evidence

ORD record
ord-dd747b72ff7944e9ad4c560b5c39d0fe
Source dataset
uspto-grants-2011_01
Patent number
US07868188B2

Reaction notes

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