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

HRID 1019944Notes

Reaction equation

HRID 1019944 reaction equation
[Cl:1][C:2]1[C:11]([C:12]([OH:14])=O)=[N:10][C:9]2[NH:8][C:7](=[O:15])[CH2:6][S:5][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:12]([C:11]3[C:2]([Cl:1])=[CH:3][C:4]4[S:5][CH2:6][C:7](=[O:15])[NH:8][C:9]=4[N:10]=3)=[O:14])[CH2:33][CH2:32]1)=[CH:21]2

Participants

3

Reactant 2

HCID 218737897-Chloro-3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazine-6-carboxylic acidHCID 667472011-[2-(6-Methoxy-quinolin-3-ylsulfanyl)-ethyl]-piperidin-4-ylamine

Product 1

HCID 468531757-chloro-3-oxo-3,4-dihydro-2H-pyrido[3,2-b][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 light yellow solid (49 mg, 91% yield) following Scheme 3 and in analogy to Example 53 using 7-chloro-3-oxo-3,4-dihydro-2H-pyrido[3,2-b][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-13aa55edd4aa4aefafbe1b48a29e1be7
Source dataset
uspto-grants-2014_05
Patent number
US08716280B2

Reaction notes

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