2-Amino-6-Chloropyrazine → N-(6-chloro-pyrazin-2-yl)-2-ethyl-4-hydroxy-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxide

HRID 484687Notes

Reaction equation

HRID 484687 reaction equation
[CH2:1]([N:3]1[C:8]([C:9]([O:11]C)=O)=[C:7]([OH:13])[C:6]2[CH:14]=[CH:15][CH:16]=[CH:17][C:5]=2[S:4]1(=[O:19])=[O:18])[CH3:2].[NH2:20][C:21]1[CH:26]=[N:25][CH:24]=[C:23]([Cl:27])[N:22]=1>C1(C)C(C)=CC=CC=1>[Cl:27][C:23]1[N:22]=[C:21]([NH:20][C:9]([C:8]2[N:3]([CH2:1][CH3:2])[S:4](=[O:19])(=[O:18])[C:5]3[CH:17]=[CH:16][CH:15]=[CH:14][C:6]=3[C:7]=2[OH:13])=[O:11])[CH:26]=[N:25][CH:24]=1

Participants

4

Reactant 2

HCID 1184582-Amino-6-ChloropyrazineHCID 54703133methyl 2-ethyl-4-hydroxy-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide

Product 1

HCID 54703125N-(6-chloro-pyrazin-2-yl)-2-ethyl-4-hydroxy-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxideYield 64%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

8.5 g (30 mmols) of methyl 2-ethyl-4-hydroxy-2H-1,2-benzothiazine-3-carboxylate-1,1-dioxide and 3.9 g (30 mmols) of 2-amino-6-chloro-pyrazine were reacted in 600 ml of xylene and worked up analogous to Example 1, yielding 7.3 g (64% of theory) of N-(6-chloro-pyrazin-2-yl)-2-ethyl-4-hydroxy-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxide.

Sources & evidence

ORD record
ord-83e04f02f7e14188b9a5a4aaca6fac0e
Source dataset
uspto-grants-1985_08
Patent number
US04533664

Reaction notes

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