3-Bromo-1-propanol → 3-oxo-3,4-dihydro-2H-benzo[1,4]thiazine-6-carboxylic acid {1-[3-(7-methoxy-quinoxalin-2-yloxy)-propyl]-azetidin-3-yl}-amide

HRID 1019869Notes

Reaction equation

HRID 1019869 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][CH2:17][OH:18].C(O[C:24](=[O:30])[NH:25][CH:26]1[CH2:29][NH:28][CH2:27]1)(C)(C)C.[O:31]=[C:32]1[NH:37][C:36]2[CH:38]=[C:39](C(O)=O)[CH:40]=[CH:41][C:35]=2[S:34][CH2:33]1>>[CH3:13][O:12][C:6]1[CH:5]=[C:4]2[C:9]([N:10]=[CH:11][C:2]([O:18][CH2:17][CH2:16][CH2:15][N:28]3[CH2:27][CH:26]([NH:25][C:24]([C:39]4[CH:40]=[CH:41][C:35]5[S:34][CH2:33][C:32](=[O:31])[NH:37][C:36]=5[CH:38]=4)=[O:30])[CH2:29]3)=[N:3]2)=[CH:8][CH:7]=1

Participants

5

Reactant 4

HCID 123083-Bromo-1-propanolHCID 7609933-oxo-3,4-dihydro-2H-1,4-benzothiazine-6-carboxylic acidHCID 15194053-Aminoazetidine, 3-BOC protectedHCID 126864152-Chloro-7-methoxyquinoxaline

Product 1

HCID 468520723-oxo-3,4-dihydro-2H-benzo[1,4]thiazine-6-carboxylic acid {1-[3-(7-methoxy-quinoxalin-2-yloxy)-propyl]-azetidin-3-yl}-amide

Procedure

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

Sources & evidence

ORD record
ord-1f22a3ce91984654a3dda8bfa640d6ca
Source dataset
uspto-grants-2014_05
Patent number
US08716280B2

Reaction notes

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