2-Aminopyridine → 2-methyl-1,1,4-trioxo-N-(2-pyridinyl)-3H-1$l^{6},2-benzothiazine-3-carboxamide

HRID 866664Notes

Reaction equation

HRID 866664 reaction equation
[CH3:1][N:2]1[CH:7]([C:8]([OH:10])=O)[C:6](=[O:11])[C:5]2[CH:12]=[CH:13][CH:14]=[CH:15][C:4]=2[S:3]1(=[O:17])=[O:16].[NH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=1.C(OC(N1C2C(=CC=CC=2)C=CC1OCC)=O)C>O1CCCC1>[N:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[NH:18][C:8]([CH:7]1[C:6](=[O:11])[C:5]2[CH:12]=[CH:13][CH:14]=[CH:15][C:4]=2[S:3](=[O:17])(=[O:16])[N:2]1[CH3:1])=[O:10]

Participants

5

Reactant 3

HCID 104392-AminopyridineHCID 278332-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinolineHCID 130512493,4-Dihydro-2-methyl-4-oxo-2H-1,2-benzothiazine-3-carboxylic Acid-1,1-dioxide

Product 1

HCID 98806202-methyl-1,1,4-trioxo-N-(2-pyridinyl)-3H-1$l^{6},2-benzothiazine-3-carboxamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3,4-dihydro-2-methyl-4-oxo-2H-1,2-benzothiazine-3-carboxylic acid-1,1-dioxide (127 mg.) and 2-aminopyridine (52 mg.) in tetrahydrofuran (5 ml.) is added, with stirring, a solution of N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline (148 mg.) in tetrahydrofuran (1 ml.). The mixture is stirred at room temperature (23°-25° C.) for four hours and is then concentrated under reduced pressure to an oil. Thin layer chromatography on silica gel plates in the system - benzene:acetic acid (95:5) and visualization of the plate under a 366 mμ lamp showed, by comparison with an authentic sample, the title compound is present.

Workup

  1. stirringThe mixture is stirred at room temperature (23°-25° C.) for four hours
  2. concentrationis then concentrated under reduced pressure to an oil

Sources & evidence

ORD record
ord-8a394238182d4830b1e72f77d359323b
Source dataset
uspto-grants-1978_07
Patent number
US04100347

Reaction notes

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