8-Quinolinamine, 1,2,3,4-tetrahydro- → 4-(2,5-Dichloro-phenoxy)-N-(1,2,3,4-tetrahydro-quinolin-8-yl)-nicotinamide

HRID 1966997Notes

Reaction equation

HRID 1966997 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].[NH:28]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][C:36]=2[NH2:38])[CH2:31][CH2:30][CH2:29]1>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]([NH:38][C:36]2[CH:35]=[CH:34][CH:33]=[C:32]3[C:37]=2[NH:28][CH2:29][CH2:30][CH2:31]3)=[O:12])=[CH:7][N:8]=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 1046728-Quinolinamine, 1,2,3,4-tetrahydro-HCID 53311781[4-(2,5-Dichloro-phenoxy)-pyridin-3-yl]-(3,4-dihydro-2H-quinolin-1-yl)-methanone

Product 1

HCID 533121074-(2,5-Dichloro-phenoxy)-N-(1,2,3,4-tetrahydro-quinolin-8-yl)-nicotinamide

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 1,2,3,4-tetrahydro-quinolin-8-ylamine (commercially available; CAS RN 54012-92-9) and using a gradient of n-heptane:ethyl acetate (100:0 to 0:100) for the chromatographic purification. Light yellow solid (88%). MS (ESI): m/z=414.077 [M+H]+.

Workup

  1. customfor the chromatographic purification

Sources & evidence

ORD record
ord-541d72de259d494d81935c5871d729b8
Source dataset
uspto-grants-2013_04
Patent number
US08420647B2

Reaction notes

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