Triethylamine → HCID 71621098, compound

HRID 1775501Notes

Reaction equation

[S:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3](=[O:10])[NH:2]1.C(N(CC)CC)C.[N:18]1([C:24](Cl)=[O:25])[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1>C(#N)C>[N:18]1([C:24]([N:2]2[C:3](=[O:10])[C:4]3[C:5](=[N:6][CH:7]=[CH:8][CH:9]=3)[S:1]2)=[O:25])[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1

Participants

Conditions

Temperature: 60 °C

Procedure

To a suspension of isothiazolo[5,4-b]pyridin-3-one (5.0 g, 32.86 mmol) in acetonitrile (180 ml) was added dropwise triethylamine (14 ml, 99 mmol) and afterwards 4-morpholinecarbonyl chloride (3.8 ml, 32.9 mmol) at room temperature. The reaction mixture was stirred for 3 h at 60° C. The solvent was removed under reduced pressure. To the crude oil was added water (50 ml) and ethyl acetate (50 ml), the phases separated and the aqueous phase extracted with ethyl acetate. The organic layers were combined, washed with water, dried over sodium sulfate, filtered and concentrated in vacuo. Purification of the residue by high performance liquid chromatography (RP silica gel, acetonitrile/water/trifluoroacetic acid) and lyophilization of the product fractions provided 5.0 g (57%) of the title compound as a white powder.

Workup

customThe solvent was removed under reduced pressure
additionTo the crude oil was added water (50 ml) and ethyl acetate (50 ml)
customthe phases separated
extractionthe aqueous phase extracted with ethyl acetate
washwashed with water
dry with materialdried over sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
customPurification of the residue by high performance liquid chromatography (RP silica gel, acetonitrile/water/trifluoroacetic acid) and lyophilization of the product fractions

Sources & evidence

ORD record: ord-89d8b7ecd9cd43bf8f0ee20c7ce2b695
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09260454B2

Reaction notes

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