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

HRID 2279327Notes

Reaction equation

HRID 2279327 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:32])[NH:25][CH2:26][CH:27]1[CH2:31][CH2:30][NH:29][CH2:28]1)(C)(C)C.[Cl:33][C:34]1[C:43](C(O)=O)=[CH:42][C:37]2[NH:38][CH2:39][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:18][CH2:17][CH2:16][CH2:15][N:29]3[CH2:30][CH2:31][CH:27]([CH2:26][NH:25][C:24]([C:43]4[C:34]([Cl:33])=[CH:35][C:36]5[S:41][CH2:40][CH2:39][NH:38][C:37]=5[CH:42]=4)=[O:32])[CH2:28]3)=[N:3]2)=[CH:8][CH:7]=1

Participants

5

Reactant 4

HCID 123083-Bromo-1-propanolHCID 4250767tert-butyl N-((pyrrolidin-3-yl)methyl)carbamateHCID 126864152-Chloro-7-methoxyquinoxalineHCID 667474747-chloro-3,4-dihydro-2H-benzo[1,4]thiazine-6-carboxylic acid

Product 1

HCID 667462947-chloro-3,4-dihydro-2H-benzo[1,4]thiazine-6-carboxylic acid {1-[3-(7-methoxy-quinoxalin-2-yloxy)-propyl]-pyrrolidin-3-ylmethyl}-amide

Procedure

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

Sources & evidence

ORD record
ord-6b28ff4f65394a4dbbec6b5af2d20f02
Source dataset
uspto-grants-2015_09
Patent number
US09133219B2

Reaction notes

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