2-Morpholinoethylamine → HCID 59867516, compound

HRID 383548Notes

Reaction equation

ClC1N=NC(C2C=CC=CC=2)=CC=1C1C=CN=CC=1.N1(CCN)CCOCC1.CN1CCN([C:36]2([NH:54][CH2:55][CH2:56][N:57]3[CH2:62][CH2:61][O:60][CH2:59][CH2:58]3)[C:41]([C:42]3[CH:47]=[CH:46][N:45]=[CH:44][CH:43]=3)=[CH:40][C:39]([C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=3)=[N:38][NH:37]2)CC1>>[O:60]1[CH2:61][CH2:62][N:57]([CH2:56][CH2:55][NH:54][C:36]2[N:37]=[N:38][C:39]([C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=3)=[CH:40][C:41]=2[C:42]2[CH:47]=[CH:46][N:45]=[CH:44][CH:43]=2)[CH2:58][CH2:59]1

Participants

Reactant 3

HCID 4082852-Morpholinoethylamine

HCID 69275909HCID 69275909, compound

HCID 86242065HCID 86242065, compound

Product 1

HCID 59867516HCID 59867516, compound

Conditions

Temperature: 130 °C

Procedure

A mixture of 3-chloro-6-phenyl-4-(pyridin-4-yl)pyridazine (MW01-7-076WH) (0.5 mmol), 2-Morpholin-4-yl-ethylamine (2.0 mmol) in 3 ml of 1-BuOH was heated with stirring at 130° C. for about 7 days. The solvent was removed by evaporation in vacuo, the residue was treated with water to give a suspension. The solid was then filtered off, washed with water, then 1:3, Ethyl Acetate:Petroleum ether, dried over filter funnel in vacuo to yield a gray solid. ESI-MS: m/z 362.2 (M+H+). A synthetic reaction scheme for the preparation of 3-(4-methylpiperazin-1-yl)-N-(2-morpholinoethyl)-6-phenyl-4-(pyridin-4-yl)pyridazin-3-amine (MW01-7-091WH) is depicted in FIG. 10.

Workup

temperaturewas heated
customThe solvent was removed by evaporation in vacuo
additionthe residue was treated with water
customto give a suspension
filtrationThe solid was then filtered off
washwashed with water
dry with material1:3, Ethyl Acetate:Petroleum ether, dried
filtrationover filter funnel in vacuo
customto yield a gray solid
customA synthetic reaction scheme

Sources & evidence

ORD record: ord-1288b427f58043569035589f0736fcc0
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08367672B2

Reaction notes

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