7-chloro-3-oxo-3,4-dihydro-2H-benzo[1,4]thiazine-6-carboxylic acid → 7-chloro-3-oxo-3,4-dihydro-2H-benzo[1,4]thiazine-6-carboxylic acid {1-[2-(6-methoxy-quinolin-3-ylsulfanyl)-ethyl]-piperidin-4-yl}-amide

HRID 2279376Notes

Reaction equation

HRID 2279376 reaction equation
[Cl:1][C:2]1[C:12]([C:13]([OH:15])=O)=[CH:11][C:5]2[NH:6][C:7](=[O:10])[CH2:8][S:9][C:4]=2[CH:3]=1.[CH3:16][O:17][C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][CH:27]=1)[N:24]=[CH:23][C:22]([S:28][CH2:29][CH2:30][N:31]1[CH2:36][CH2:35][CH:34]([NH2:37])[CH2:33][CH2:32]1)=[CH:21]2>>[CH3:16][O:17][C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][CH:27]=1)[N:24]=[CH:23][C:22]([S:28][CH2:29][CH2:30][N:31]1[CH2:36][CH2:35][CH:34]([NH:37][C:13]([C:12]3[C:2]([Cl:1])=[CH:3][C:4]4[S:9][CH2:8][C:7](=[O:10])[NH:6][C:5]=4[CH:11]=3)=[O:15])[CH2:33][CH2:32]1)=[CH:21]2

Participants

3

Reactant 2

HCID 595606347-chloro-3-oxo-3,4-dihydro-2H-benzo[1,4]thiazine-6-carboxylic acidHCID 667472011-[2-(6-Methoxy-quinolin-3-ylsulfanyl)-ethyl]-piperidin-4-ylamine

Product 1

HCID 468531747-chloro-3-oxo-3,4-dihydro-2H-benzo[1,4]thiazine-6-carboxylic acid {1-[2-(6-methoxy-quinolin-3-ylsulfanyl)-ethyl]-piperidin-4-yl}-amide

Procedure

The title compound is prepared as a white solid (13 mg, 24% yield) following Scheme 3 and in analogy to Example 53 using 7-chloro-3-oxo-3,4-dihydro-2H-benzo[1,4]thiazine-6-carboxylic acid (22 mg, 0.09 mmol, 1.0 eq) and 1-[2-(6-methoxy-quinolin-3-ylsulfanyl)-ethyl]-piperidin-4-ylamine (30 mg, 0.09 mmol, 1.0 eq) as starting materials.

Sources & evidence

ORD record
ord-fbaf126d3edf446db60959e6e9c4810e
Source dataset
uspto-grants-2015_09
Patent number
US09133219B2

Reaction notes

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