Ethyl 3-(4-pyridyl)-3-oxopropionate → (+/-) 2-(1-Methyl-5-oxo-7-pyrimidin-4-yl-1,2,3,4,4a,5-hexahydronaphthalen-1-yl)-1H-isoindole-1,3(2H)-dione

HRID 217891Notes

Reaction equation

HRID 217891 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7](=O)[CH2:8][C:9]([O:11]CC)=O)=[N:3][CH:2]=1.N1C=[CH:19][C:18](C(=O)CC(OCC)=O)=[CH:17][CH:16]=1.Cl.NC1[C:36]([N:38]2[C:46](=[O:47])[C:45]3[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=3)[C:39]2=[O:48])([CH3:37])[CH2:35][CH2:34]CN=1>>[CH3:37][C:36]1([N:38]2[C:46](=[O:47])[C:45]3[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=3)[C:39]2=[O:48])[C:35]2[CH:19]([C:9](=[O:11])[CH:8]=[C:7]([C:4]3[CH:5]=[CH:6][N:1]=[CH:2][N:3]=3)[CH:34]=2)[CH2:18][CH2:17][CH2:16]1

Participants

4

Reactant 3

HCID 2735202Ethyl 3-(4-pyridyl)-3-oxopropionateHCID 11961458Ethyl 3-oxo-3-(pyrimidin-4-yl)propanoateHCID 67265817HCID 67265817, compound

Product 1

HCID 67265612(+/-) 2-(1-Methyl-5-oxo-7-pyrimidin-4-yl-1,2,3,4,4a,5-hexahydronaphthalen-1-yl)-1H-isoindole-1,3(2H)-dione

Procedure

By analogy with the method described in example 1 (step 1.3), using ethyl 3-(4-pyrimidinyl)-3-oxopropionate (prepared by analogy to the method described in patent DE 2705582) in place of ethyl 3-(pyridin-4-yl)-3-oxopropionate and using 2-(2-amino-3-methyl-3,4,5,6-tetrahydropyridin-3-yl)-1H-isoindole-1,3(2H)-dione hydrochloride (1:1) the compound was obtained as a white powder.

Workup

  1. customprepared by analogy to the method
  2. customwas obtained as a white powder

Sources & evidence

ORD record
ord-844996f07d1e4f3ea823a5132f15984f
Source dataset
uspto-grants-2012_06
Patent number
US08198287B2

Reaction notes

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