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

HRID 1967060Notes

Reaction equation

HRID 1967060 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.[NH:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[NH:22][CH2:21][CH2:20]1>>[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:19]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[NH:22][CH2:21][CH2:20]2)=[O:13])=[CH:9][N:8]=[CH:7][N:6]=1

Participants

3

Reactant 2

HCID 770281,2,3,4-TetrahydroquinoxalineHCID 673202614-(2,5-Dichloro-phenoxy)-pyrimidine-5-carboxylic acid

Product 1

HCID 53311620[4-(2,5-Dichloro-phenoxy)-pyrimidin-5-yl]-(3,4-dihydro-2H-quinoxalin-1-yl)-methanoneYield 20%

Procedure

The title compound was prepared in analogy to Example 77, from 4-(2,5-dichloro-phenoxy)-pyrimidine-5-carboxylic acid (Example 76, intermediate a) and 1,2,3,4-tetrahydroquinoxaline (commercially available, CAS RN 3476-89-9). The compound was purified by preparative HPLC (Phenomenex Gemini column) using a gradient of acetonitrile:water (10:90 to 98:2) to give 16 mg (20%) of the desired compound. MS (ESI): m/z=401.0 [M+H]+.

Workup

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

Sources & evidence

ORD record
ord-6a488f5ac9dc4e868ca9a50ae4fedeac
Source dataset
uspto-grants-2013_04
Patent number
US08420647B2

Reaction notes

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