Ethyl isocyanate → HCID 57344635, compound

HRID 2401400Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[C:12]3[C:19]([CH3:22])=[N:20][O:21][C:11]=3[CH:10]([NH2:23])[N:9]=2)=[CH:4][CH:3]=1.[CH2:24]([N:26]=[C:27]=[O:28])[CH3:25].C(N(CC)CC)C>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[C:12]3[C:19]([CH3:22])=[N:20][O:21][C:11]=3[CH:10]([NH:23][C:27]([NH:26][CH2:24][CH3:25])=[O:28])[N:9]=2)=[CH:4][CH:3]=1

Participants

Reactant 3

HCID 8022Ethyl isocyanate

HCID 8471Triethylamine

HCID 57344512HCID 57344512, compound

Product 1

HCID 57344635HCID 57344635, compoundYield 83.2%

Conditions

Temperature: 0 °C

Procedure

To a round bottomed flask was added 6-(4-chlorophenyl)-1-methyl-4H-benzo[c]isoxazolo[4,5-e]azepin-4-amine (218 mg, 0.67 mmol). The flask was purged with nitrogen, MeCN was added (7 mL), and the solution was cooled to 0° C. Ethyl isocyanate (128 μL, 1.62 mmol) and triethylamine (244 μL, 1.75 mmol) were added and the reaction was allowed to warm to ambient temperature and stirred for 2 h. The reaction was quenched with a 1:1 mixture of sat. aq. NaHCO3:brine and extracted with EtOAc. The organic layer was dried over Na2SO4, filtered, concentrated and purified on a Biotage (isocratic elution 40% EtOAc: 60% Hexanes) to provide the title compound as white solid (220 mg). LC/MS m/z 395 [M+H]+.

Workup

customThe flask was purged with nitrogen, MeCN
additionwas added (7 mL)
temperatureto warm to ambient temperature
customThe reaction was quenched with a 1:1 mixture of sat. aq. NaHCO3
extractionbrine and extracted with EtOAc
dry with materialThe organic layer was dried over Na2SO4
filtrationfiltered
concentrationconcentrated
custompurified on a Biotage (isocratic elution 40% EtOAc: 60% Hexanes)

Sources & evidence

ORD record: ord-e636b0cbc297419ab71fe54fb28b2aea
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08796261B2

Reaction notes

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