[4-(2,5-Dichloro-phenoxy)-pyridin-3-yl]-(3,4-dihydro-2H-quinolin-1-yl)-methanone → (6-Chloro-4-cyclopropyl-7-fluoro-3,4-dihydro-2H-quinoxalin-1-yl)[4-(2,5-dichloro-phenoxy)-pyridin-3-yl]-methanone

HRID 1025826Notes

Reaction equation

HRID 1025826 reaction equation
[Cl:1][C:2]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[CH:7][C:6]=1[C:11](N1C2C(=CC=CC=2)CCC1)=[O:12].[Cl:28][C:29]1[CH:38]=[C:37]2[C:32]([NH:33][CH2:34][CH2:35][N:36]2[CH:39]2[CH2:41][CH2:40]2)=[CH:31][C:30]=1[F:42]>CCCCCCC.C(OCC)(=O)C>[Cl:28][C:29]1[CH:38]=[C:37]2[C:32](=[CH:31][C:30]=1[F:42])[N:33]([C:11]([C:6]1[CH:7]=[N:8][CH:9]=[CH:10][C:5]=1[O:4][C:3]1[CH:23]=[C:24]([Cl:27])[CH:25]=[CH:26][C:2]=1[Cl:1])=[O:12])[CH2:34][CH2:35][N:36]2[CH:39]1[CH2:41][CH2:40]1

Participants

4

Reactant 2

HCID 53311781[4-(2,5-Dichloro-phenoxy)-pyridin-3-yl]-(3,4-dihydro-2H-quinolin-1-yl)-methanoneHCID 673208217-Chloro-1-cyclopropyl-6-fluoro-1,2,3,4-tetrahydroquinoxaline

Product 1

HCID 53311950(6-Chloro-4-cyclopropyl-7-fluoro-3,4-dihydro-2H-quinoxalin-1-yl)[4-(2,5-dichloro-phenoxy)-pyridin-3-yl]-methanone

Reagents, catalysts & solvents 1

HCID 21899848Ethylacetate heptaneSolvent

Procedure

The title compound was prepared in analogy to Example 1, from 4-(2,5-dichloro-phenoxy)-nicotinic acid (Example 1, intermediate) and 7-chloro-1-cyclopropyl-6-fluoro-1,2,3,4-tetrahydro-quinoxaline and using a gradient of n-heptane:ethyl acetate (100:0 to 0:100) for the chromatographic purification. Light yellow solid (19%). MS (ESI): m/z=494.041 [M+H]+.

Workup

  1. customfor the chromatographic purification

Sources & evidence

ORD record
ord-c2b15d7264324df8b8c2e7a29c25464e
Source dataset
uspto-grants-2014_05
Patent number
US08729091B2

Reaction notes

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