N-(3-Aminopropyl)morpholine → 1-(4-Cyano-3-(4-nitrophenyl)isothiazol-5-yl)-3-(3-morpholinopropyl)urea

HRID 870991Notes

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].[O:27]1[CH2:32][CH2:31][N:30]([CH2:33][CH2:34][CH2:35][NH2:36])[CH2:29][CH2:28]1>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:36][CH2:35][CH2:34][CH2:33][N:30]1[CH2:31][CH2:32][O:27][CH2:28][CH2:29]1)=[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-morpholinopropylamine (0.021 mL, 0.14 mmol) in 0.8 mL dioxane was heated at 80° C. After 2 hours the reaction mixture was evaporated to a yellowish oily film. This material was then chromatographed eluting with EtOAc, then gradient 2% to 6% MeOH in EtOAc to give the title compound as a pale yellow solid (33 mg, 80%). 1H NMR (acetone) δ: 8.38-8.44 (m, 2H), 8.22-8.27 (m, 2H), 6.91 (t, J=5.4 Hz, 1H), 3.59-3.64 (m, 4H), 3.38-3.45 (m, 2H), 2.37-2.45 (m, 6H), 1.77 (quin, J=6.8 Hz, 2H)

Workup

customAfter 2 hours the reaction mixture was evaporated to a yellowish oily film
customThis material was then chromatographed
washeluting with EtOAc

Sources & evidence

ORD record: ord-b8767c52b37c4c5a8dabd9d9b86f1b79
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969583B2

Reaction notes

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