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

HRID 484688Notes

Reaction equation

HRID 484688 reaction equation
[CH2:1]([N:4]1[C:9]([C:10]([O:12]C)=O)=[C:8]([OH:14])[C:7]2[CH:15]=[CH:16][CH:17]=[CH:18][C:6]=2[S:5]1(=[O:20])=[O:19])[CH2:2][CH3:3].[NH2:21][C:22]1[CH:27]=[N:26][CH:25]=[C:24]([Cl:28])[N:23]=1>C1(C)C(C)=CC=CC=1>[Cl:28][C:24]1[N:23]=[C:22]([NH:21][C:10]([C:9]2[N:4]([CH2:1][CH2:2][CH3:3])[S:5](=[O:20])(=[O:19])[C:6]3[CH:18]=[CH:17][CH:16]=[CH:15][C:7]=3[C:8]=2[OH:14])=[O:12])[CH:27]=[N:26][CH:25]=1

Participants

4

Reactant 2

HCID 1184582-Amino-6-ChloropyrazineHCID 54703140Methyl 4-hydroxy-2-propyl-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide

Product 1

HCID 54703123N-(6-chloro-pyrazin-2-yl)-4-hydroxy-2-n-propyl-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxideYield 52%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

2.97 g (10 mmols) of methyl 2-n-propyl-4-hydroxy-2H-1,2-benzothiazine-3-carboxylate-1,1-dioxide and 1.3 g (10 mmols) of 2-amino-6-chloro-pyrazine were reacted in 150 ml of xylene analogous to Example 1, yielding 2.05 g (52% of theory) of N-(6-chloro-pyrazin-2-yl)-4-hydroxy-2-n-propyl-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxide.

Sources & evidence

ORD record
ord-0867c641bf6348c59f4dcd76a87d379e
Source dataset
uspto-grants-1985_08
Patent number
US04533664

Reaction notes

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