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-(7-methoxy-quinoxalin-2-ylsulfanyl)-ethyl]-piperidin-4-yl}-amide

HRID 1019919Notes

Reaction equation

HRID 1019919 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:27]=[C:26]2[C:21]([N:22]=[CH:23][C:24]([S:28][CH2:29][CH2:30][N:31]3[CH2:36][CH2:35][CH:34]([NH2:37])[CH2:33][CH2:32]3)=[N:25]2)=[CH:20][CH:19]=1>>[CH3:16][O:17][C:18]1[CH:27]=[C:26]2[C:21]([N:22]=[CH:23][C:24]([S:28][CH2:29][CH2:30][N:31]3[CH2:32][CH2:33][CH:34]([NH:37][C:13]([C:12]4[C:2]([Cl:1])=[CH:3][C:4]5[S:9][CH2:8][C:7](=[O:10])[NH:6][C:5]=5[CH:11]=4)=[O:15])[CH2:35][CH2:36]3)=[N:25]2)=[CH:20][CH:19]=1

Participants

3

Reactant 2

HCID 595606347-chloro-3-oxo-3,4-dihydro-2H-benzo[1,4]thiazine-6-carboxylic acidHCID 667465301-[2-(7-Methoxy-quinoxalin-2-ylsulfanyl)-ethyl]-piperidin-4-ylamine

Product 1

HCID 468359137-chloro-3-oxo-3,4-dihydro-2H-benzo[1,4]thiazine-6-carboxylic acid {1-[2-(7-methoxy-quinoxalin-2-ylsulfanyl)-ethyl]-piperidin-4-yl}-amide

Procedure

The title compound is prepared as an off-white solid (42 mg, 60% yield) following Scheme 3 and in analogy to Example 35 using 7-chloro-3-oxo-3,4-dihydro-2H-benzo[1,4]thiazine-6-carboxylic acid (31 mg, 0.12 mmol 1.0 eq) and 1-[2-(7-methoxy-quinoxalin-2-ylsulfanyl)-ethyl]-piperidin-4-ylamine (40 mg, 0.12 mmol, 1.0 eq) as starting materials.

Sources & evidence

ORD record
ord-ba6d33ea6ab34b1ca92040715a7cc11b
Source dataset
uspto-grants-2014_05
Patent number
US08716280B2

Reaction notes

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