2-Bromoethanol → 7-chloro-3-oxo-3,4-dihydro-2H-benzo[1,4]thiazine-6-carboxylic acid {1-[2-(7-methoxy-quinoxalin-2-yloxy)-ethyl]-piperidin-4-ylmethyl}-amide

HRID 1019890Notes

Reaction equation

HRID 1019890 reaction equation
Cl[C:2]1[CH:11]=[N:10][C:9]2[C:4](=[CH:5][C:6]([O:12][CH3:13])=[CH:7][CH:8]=2)[N:3]=1.Br[CH2:15][CH2:16][OH:17].C(O[C:23](=[O:32])[NH:24][CH2:25][CH:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1)(C)(C)C.[Cl:33][C:34]1[C:44](C(O)=O)=[CH:43][C:37]2[NH:38][C:39](=[O:42])[CH2:40][S:41][C:36]=2[CH:35]=1>>[CH3:13][O:12][C:6]1[CH:5]=[C:4]2[C:9]([N:10]=[CH:11][C:2]([O:17][CH2:16][CH2:15][N:29]3[CH2:28][CH2:27][CH:26]([CH2:25][NH:24][C:23]([C:44]4[C:34]([Cl:33])=[CH:35][C:36]5[S:41][CH2:40][C:39](=[O:42])[NH:38][C:37]=5[CH:43]=4)=[O:32])[CH2:31][CH2:30]3)=[N:3]2)=[CH:8][CH:7]=1

Participants

5

Reactant 4

HCID 108982-BromoethanolHCID 723429Tert-butyl (piperidin-4-ylmethyl)carbamateHCID 126864152-Chloro-7-methoxyquinoxalineHCID 595606347-chloro-3-oxo-3,4-dihydro-2H-benzo[1,4]thiazine-6-carboxylic acid

Product 1

HCID 667474417-chloro-3-oxo-3,4-dihydro-2H-benzo[1,4]thiazine-6-carboxylic acid {1-[2-(7-methoxy-quinoxalin-2-yloxy)-ethyl]-piperidin-4-ylmethyl}-amide

Procedure

The title compound is prepared as an off-white solid following Scheme 1 and in analogy to Example 1 using 2-chloro-7-methoxy-quinoxaline, 2-bromo-ethanol, piperidin-4-ylmethyl-carbamic acid tert-butyl ester and 7-chloro-3-oxo-3,4-dihydro-2H-benzo[1,4]thiazine-6-carboxylic acid as starting materials.

Sources & evidence

ORD record
ord-e55b01cbccf240db9217117b778eddbc
Source dataset
uspto-grants-2014_05
Patent number
US08716280B2

Reaction notes

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