Water → HCID 178517471, compound

HRID 2389810Notes

Reaction equation

[C:1]([CH:3]=[C:4]([NH:15][C:16](=[O:20])OCC)[C:5]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:7][CH:6]=1)#[N:2].[N:21]1([CH2:27][C:28]([NH:30][NH2:31])=O)[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1.C(OCC)(=O)C.O>CN1C(=O)CCC1>[N:21]1([CH2:27][C:28]2[N:2]=[C:1]3[N:31]([C:16]([OH:20])=[N:15][C:4]([C:5]4[CH:6]=[CH:7][C:8]([C:11]([F:12])([F:13])[F:14])=[CH:9][CH:10]=4)=[CH:3]3)[N:30]=2)[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1

Participants

Conditions

Temperature: 190 °C

Procedure

2.4 g (8.4 mmol) of ethyl {2-cyano-1-[4-(trifluoromethyl)phenyl]ethenyl}carbamate (Example 129A) and 1.34 g (8.4 mmol) of 2-morpholin-4-ylacetohydrazide are dissolved in NMP (12 ml) and stirred in a flask with a calcium chloride drying tube at an oil-bath temperature of 190° C. for 4 h. The reaction mixture is cooled to RT and ethyl acetate (150 ml) and water (100 ml) are added. The organic phase is washed with saturated sodium bicarbonate solution, separated off, dried with magnesium sulphate and concentrated. The residue is chromatographed on silica gel (mobile phase cyclohexane/ethyl acetate 10:1 to 1:1, then with dichloromethane/methanol 100:1). 850 mg (26% of theory) of the product are obtained.

Workup

temperatureThe reaction mixture is cooled to RT
washThe organic phase is washed with saturated sodium bicarbonate solution
customseparated off
dry with materialdried with magnesium sulphate
concentrationconcentrated
customThe residue is chromatographed on silica gel (mobile phase cyclohexane/ethyl acetate 10:1 to 1:1
custom850 mg (26% of theory) of the product are obtained

Sources & evidence

ORD record: ord-9060d52338e14955b4cb88ca85c6ff58
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08273752B2

Reaction notes

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