Sodium hydride → (R)-8-(1-Isopropyl-piperidin-4-yloxy)-4-methyl-2-(5-methyl-3-phenyl-isoxazol-4-ylmethyl)-3,4-dihydro-2H-pyrazino[1,2-a]indol-1-one

HRID 506721Notes

Reaction equation

HRID 506721 reaction equation
[CH:1]([N:4]1[CH2:9][CH2:8][CH:7]([O:10][C:11]2[CH:19]=[CH:18][C:17]3[N:16]4[C@H:20]([CH3:25])[CH2:21][NH:22][C:23](=[O:24])[C:15]4=[CH:14][C:13]=3[CH:12]=2)[CH2:6][CH2:5]1)([CH3:3])[CH3:2].[H-].[Na+].Br[CH2:29][C:30]1[C:31]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[N:32][O:33][C:34]=1[CH3:35]>>[CH:1]([N:4]1[CH2:9][CH2:8][CH:7]([O:10][C:11]2[CH:19]=[CH:18][C:17]3[N:16]4[C@H:20]([CH3:25])[CH2:21][N:22]([CH2:29][C:30]5[C:31]([C:36]6[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=6)=[N:32][O:33][C:34]=5[CH3:35])[C:23](=[O:24])[C:15]4=[CH:14][C:13]=3[CH:12]=2)[CH2:6][CH2:5]1)([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 27761474-(Bromomethyl)-5-methyl-3-phenylisoxazoleHCID 16679612(R)-8-(1-isopropylpiperidin-4-yloxy)-4-methyl-3,4-dihydropyrazino[1,2-a]indol-1(2H)-one

Product 1

HCID 68462831(R)-8-(1-Isopropyl-piperidin-4-yloxy)-4-methyl-2-(5-methyl-3-phenyl-isoxazol-4-ylmethyl)-3,4-dihydro-2H-pyrazino[1,2-a]indol-1-oneYield 71%

Procedure

The title compound was synthesized in analogy to example 17, from (R)-8-(1-isopropyl-piperidin-4-yloxy)-4-methyl-3,4-dihydro-2H-pyrazino[1,2-a]indol-1-one (example 8), sodium hydride and 4-(bromomethyl)-5-methyl-3-phenylisoxazol, to give the desired product as a brown oil (71%).

Sources & evidence

ORD record
ord-eda9d696a4d948959b92eee9d89567f2
Source dataset
uspto-grants-2010_08
Patent number
US07786109B2

Reaction notes

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