Diethyl Ether → 6-Cyclobutyloxy-3,4-dimethoxy-[1-(5-methanesulfonamido-1,2,3,4-tetrahydroisoquinol-2-yl)ethylideneamino]benzonitrile

HRID 1004037Notes

Reaction equation

HRID 1004037 reaction equation
[C:1]([C:3]1[C:9]([O:10][CH:11]2[CH2:14][CH2:13][CH2:12]2)=[C:8](OC)[C:7]([O:17][CH3:18])=[CH:6][C:4]=1[NH2:5])#[N:2].[C:19]([N:22]1[CH2:31][CH2:30][C:29]2[C:24](=[CH:25][CH:26]=[CH:27][C:28]=2[NH:32][S:33]([CH3:36])(=[O:35])=[O:34])[CH2:23]1)(=O)[CH3:20].[CH2:37]([O:39]CC)C>>[CH:11]1([O:10][C:9]2[C:3]([C:1]#[N:2])=[C:4]([N:5]=[C:19]([N:22]3[CH2:31][CH2:30][C:29]4[C:24](=[CH:25][CH:26]=[CH:27][C:28]=4[NH:32][S:33]([CH3:36])(=[O:35])=[O:34])[CH2:23]3)[CH3:20])[C:6]([O:39][CH3:37])=[C:7]([O:17][CH3:18])[CH:8]=2)[CH2:12][CH2:13][CH2:14]1

Participants

4

Reactant 3

HCID 3283Diethyl EtherHCID 184706542-Cyano-3-cyclobutyloxy-4,5-dimethoxyanilineHCID 187684882-Acetyl-5-methanesulfonamido-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 184706436-Cyclobutyloxy-3,4-dimethoxy-[1-(5-methanesulfonamido-1,2,3,4-tetrahydroisoquinol-2-yl)ethylideneamino]benzonitrileYield 85%

Procedure

The subtitle compound was prepared from 2-cyano-3-cyclobutyloxy-4,5-dimethoxyaniline and 2-acetyl-5-methanesulfonamido-1,2,3,4-tetrahydroisoquinoline following the procedure described in Example 10(g). Trituration with diethyl ether afforded the subtitle compound as a colourless solid (85%). Rf 0.14 (ethyl acetate:hexane 1: 1, v/v).

Sources & evidence

ORD record
ord-d252d4ef4c104206882e291a4380ff92
Source dataset
uspto-grants-2000_04
Patent number
US06048864

Reaction notes

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