2-Bromoethanol → 5-Thiophen-2-yl-isoxazole-3-carboxylic acid {1-[2-(7-methoxy-quinoxalin-2-yloxy)-ethyl]-pyrrolidin-3-ylmethyl}-amide

HRID 1019893Notes

Reaction equation

HRID 1019893 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:31])[NH:24][CH2:25][CH:26]1[CH2:30][CH2:29][NH:28][CH2:27]1)(C)(C)C.[S:32]1[CH:36]=[CH:35][CH:34]=[C:33]1[C:37]1[O:41][N:40]=[C:39](C(O)=O)[CH:38]=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:28]3[CH2:29][CH2:30][CH:26]([CH2:25][NH:24][C:23]([C:39]4[CH:38]=[C:37]([C:33]5[S:32][CH:36]=[CH:35][CH:34]=5)[O:41][N:40]=4)=[O:31])[CH2:27]3)=[N:3]2)=[CH:8][CH:7]=1

Participants

5

Reactant 4

HCID 108982-BromoethanolHCID 31570985-(Thiophen-2-yl)-1,2-oxazole-3-carboxylic acidHCID 4250767tert-butyl N-((pyrrolidin-3-yl)methyl)carbamateHCID 126864152-Chloro-7-methoxyquinoxaline

Product 1

HCID 667473975-Thiophen-2-yl-isoxazole-3-carboxylic acid {1-[2-(7-methoxy-quinoxalin-2-yloxy)-ethyl]-pyrrolidin-3-ylmethyl}-amide

Procedure

The title compound is prepared as an orange semi-solid following Scheme 1 and in analogy to Example 1 using 2-chloro-7-methoxy-quinoxaline, 2-bromo-ethanol, pyrrolidin-3-ylmethyl-carbamic acid tert-butyl ester and 5-thiophen-2-yl-isoxazole-3-carboxylic acid as starting materials.

Sources & evidence

ORD record
ord-f95a0b5d4b4a4f06bc15de7b9d1f8ff6
Source dataset
uspto-grants-2014_05
Patent number
US08716280B2

Reaction notes

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