3-Methoxypropylamine → 1-(4-Cyano-3-(4-nitrophenyl)isothiazol-5-yl)-3-(3-methoxypropyl)urea

HRID 870996Notes

Reaction equation

[C:1]([C:3]1[C:4]([C:18]2[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=2)=[N:5][S:6][C:7]=1[NH:8][C:9](=[O:17])OC1C=CC=CC=1)#[N:2].[CH3:27][O:28][CH2:29][CH2:30][CH2:31][NH2:32]>O1CCOCC1>[C:1]([C:3]1[C:4]([C:18]2[CH:19]=[CH:20][C:21]([N+:24]([O-:26])=[O:25])=[CH:22][CH:23]=2)=[N:5][S:6][C:7]=1[NH:8][C:9]([NH:32][CH2:31][CH2:30][CH2:29][O:28][CH3:27])=[O:17])#[N:2]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of phenyl (4-cyano-3-(4-nitrophenyl)isothiazol-5-yl)carbamate (37 mg, 0.10 mmol) and 3-methoxypropylamine (0.015 mL, 0.15 mmol) in 0.8 mL dioxane was heated at 80° C. After 2 hours the reaction mixture was evaporated to a solid film. The solid was triturated with dichloromethane and then 10% EtOAc in hexane to give a yellow-orange solid. This material was then chromatographed eluting with gradient 50% to 70% EtOAc in hexane. The filtrate from trituration and material from another reaction were combined and chromatographed with EtOAc/hexane. The clean product lots were combined to give the title compound as an off-white solid (27 mg).

Workup

customAfter 2 hours the reaction mixture was evaporated to a solid film
customThe solid was triturated with dichloromethane
custom10% EtOAc in hexane to give a yellow-orange solid
customThis material was then chromatographed
washeluting with gradient 50% to 70% EtOAc in hexane
customchromatographed with EtOAc/hexane

Sources & evidence

ORD record: ord-f78bb9e931c24b6c875148cdc31d8a1a
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969583B2

Reaction notes

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