3-Bromo-1-propanol → 6-({1-[3-(7-methoxy-quinoxalin-2-yloxy)-propyl]-piperidin-3-ylamino}-methyl)-4H-benzo[1,4]thiazin-3-one

HRID 1019875Notes

Reaction equation

HRID 1019875 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)[NH:25][CH:26]1[CH2:31][CH2:30][CH2:29][NH:28][CH2:27]1)(C)(C)C.[O:33]=[C:34]1[NH:39][C:38]2[CH:40]=[C:41](C=O)[CH:42]=[CH:43][C:37]=2[S:36][CH2:35]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[CH2:29][CH2:30][CH2:31][CH:26]([NH:25][CH2:24][C:41]4[CH:42]=[CH:43][C:37]5[S:36][CH2:35][C:34](=[O:33])[NH:39][C:38]=5[CH:40]=4)[CH2:27]3)=[N:3]2)=[CH:8][CH:7]=1

Participants

5

Reactant 4

HCID 123083-Bromo-1-propanolHCID 42330413-(Boc-amino)piperidineHCID 109433483-Oxo-3,4-dihydro-2H-1,4-benzothiazine-6-carbaldehydeHCID 126864152-Chloro-7-methoxyquinoxaline

Product 1

HCID 667461416-({1-[3-(7-methoxy-quinoxalin-2-yloxy)-propyl]-piperidin-3-ylamino}-methyl)-4H-benzo[1,4]thiazin-3-one

Procedure

The title compound is prepared as a yellow amorphous lyophilizated solid following Scheme 1 and in analogy to Examples 1 and 9 using 2-chloro-7-methoxy-quinoxaline, 3-bromo-propan-1-ol, piperidin-3-yl-carbamic acid tert-butyl ester and 3-oxo-3,4-dihydro-2H-benzo[1,4]thiazine-6-carbaldehyde as starting materials.

Sources & evidence

ORD record
ord-73c70059149e42d9bf95e59f8994e2e2
Source dataset
uspto-grants-2014_05
Patent number
US08716280B2

Reaction notes

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