(-)-Carnitine → [4-(2,5-Dichloro-phenoxy)-pyrimidin-5-yl]-(4-methyl-3,4-dihydro-2H-quinoxalin-1-yl)-methanone

HRID 1967061Notes

Reaction equation

HRID 1967061 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:3]=1[O:4][C:5]1[C:10]([C:11]([OH:13])=O)=[CH:9][N:8]=[CH:7][N:6]=1.[CH3:19][N:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[NH:23][CH2:22][CH2:21]1.C[N+](C[C@H](O)CC([O-])=O)(C)C>>[Cl:1][C:2]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:3]=1[O:4][C:5]1[C:10]([C:11]([N:23]2[C:24]3[C:29](=[CH:28][CH:27]=[CH:26][CH:25]=3)[N:20]([CH3:19])[CH2:21][CH2:22]2)=[O:13])=[CH:9][N:8]=[CH:7][N:6]=1

Participants

4

Reactant 3

HCID 10917(-)-CarnitineHCID 2158501-Methyl-1,2,3,4-tetrahydroquinoxalineHCID 673202614-(2,5-Dichloro-phenoxy)-pyrimidine-5-carboxylic acid

Product 1

HCID 53311701[4-(2,5-Dichloro-phenoxy)-pyrimidin-5-yl]-(4-methyl-3,4-dihydro-2H-quinoxalin-1-yl)-methanoneYield 8%

Procedure

The title compound was prepared in analogy to Example 77, from 4-(2,5-dichloro-phenoxy)-pyrimidine-5-carboxylic acid and 1-methyl-1,2,3,4-tetrahydroquinoxaline (commercially available, Metina, catalog number M-636). The compound was purified by preparative HPLC (Phenomenex Gemini column) using a gradient of acetonitrile:water (10:90 to 98:2) to give 6.5 mg (8%) of the desired compound. MS (ESI): m/z=415.1 [M+H]+.

Workup

  1. customThe compound was purified by preparative HPLC (Phenomenex Gemini column)

Sources & evidence

ORD record
ord-cedbe2877d9c4bcbb9c00fe4fc0a1e07
Source dataset
uspto-grants-2013_04
Patent number
US08420647B2

Reaction notes

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