Ammonium thiocyanate → Ethyl 4-[methyl(4-oxo-4H-pyrido[3,2-e]-1,3-thiazin-2-yl)amino]benzoate

HRID 367165Notes

Reaction equation

HRID 367165 reaction equation
Cl[C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[S-:11][C:12]#[N:13].[NH4+].[CH3:15][NH:16][C:17]1[CH:27]=[CH:26][C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:19][CH:18]=1>>[CH3:15][N:16]([C:17]1[CH:27]=[CH:26][C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:19][CH:18]=1)[C:12]1[S:11][C:2]2[N:10]=[CH:9][CH:8]=[CH:7][C:3]=2[C:4](=[O:5])[N:13]=1

Participants

4

Reactant 3

HCID 15666Ammonium thiocyanateHCID 319832ethyl 4-(methylamino)benzoateHCID 27745412-Chloronicotinoyl chloride

Product 1

HCID 23287619Ethyl 4-[methyl(4-oxo-4H-pyrido[3,2-e]-1,3-thiazin-2-yl)amino]benzoateYield 88.8%

Procedure

The reaction procedure of Example 57 was followed except that 162 mg of 2-chloronicotinoyl chloride, 72 mg of ammonium thiocyanate and 169 mg of ethyl 4-(methylamino)benzoate were used. As a result, 279 mg of ethyl 4-[N-methyl-N-(4-oxo-4H-pyrido[3,2-e]-1,3-thiazin-2-yl)amino]benzoate was obtained.

Workup

  1. customThe reaction procedure of Example 57

Sources & evidence

ORD record
ord-10050d6ccbfc457a835e090e6993c95b
Source dataset
uspto-grants-2000_10
Patent number
US06133258

Reaction notes

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