2-Methoxy-N-methylaniline → HCID 53311954, compound

HRID 1025834Notes

Reaction equation

HRID 1025834 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]([N:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)CC[CH2:14]1)=[O:12].[CH3:28][O:29]C1C=CC=CC=1NC>CCCCCCC.C(OCC)(=O)C>[Cl:1][C:2]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:3]=1[O:4][C:5]1[C:6]([C:11]([N:13]([C:22]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[O:29][CH3:28])[CH3:14])=[O:12])=[CH:7][N:8]=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 27595792-Methoxy-N-methylanilineHCID 53311781[4-(2,5-Dichloro-phenoxy)-pyridin-3-yl]-(3,4-dihydro-2H-quinolin-1-yl)-methanone

Product 1

HCID 53311954HCID 53311954, compound

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 2-methoxy-N-methylaniline (commercially available; CAS RN 10541-78-3) and using a gradient of n-heptane:ethyl acetate (100:0 to 40:60). The compound was further purified through a second preparative HPLC chromatography (Phenomenex Gemini column) using a gradient of acetonitrile:water (containing 0.05% formic acid) (50:50 to 95:5). White solid (57%). MS (ESI): m/z=403.062 [M+H]+.

Workup

  1. customThe compound was further purified through a second preparative HPLC chromatography (Phenomenex Gemini column)

Sources & evidence

ORD record
ord-21d7374efd1a4024a4729c7b6c4aa90a
Source dataset
uspto-grants-2014_05
Patent number
US08729091B2

Reaction notes

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