Triethylamine → HCID 42630483, compound

HRID 1696764Notes

Reaction equation

[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([S:10]([NH2:13])(=[O:12])=[O:11])=[CH:2]1.C(N(CC)CC)C.Cl[C:22](OC1C=CC=CC=1)=[O:23].[Br:31][C:32]1[CH:37]=[C:36]([NH2:38])[N:35]=[C:34]([NH2:39])[CH:33]=1>C(#N)C>[NH2:38][C:36]1[N:35]=[C:34]([NH:39][C:22]([NH:13][S:10]([C:3]2[C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[O:1][CH:2]=2)(=[O:12])=[O:11])=[O:23])[CH:33]=[C:32]([Br:31])[CH:37]=1

Participants

Conditions

Temperature: 60 °C

Procedure

The below prepared benzofuran-3-sulfonic acid amide (0.051 g, 0.259 mmol) was dissolved in 1.5 mL of abs. acetonitrile and treated successively with triethylamine (0.090 mL, 2.5 eq.) and phenyl chloroformate (0.0405 g, 1.0 eq.), and the mixture was then kept at ambient temperature for 1 h. 4-Bromo-pyridine-2,6-diamine (0.0486 g, 1.0 eq.), dissolved in a tiny amount of acetonitrile, was added, and the mixture heated to 60° C. for 18 h. Cooling, pouring onto crashed ice, twofold extraction with AcOEt, washing with water, drying over sodium sulfate, and evaporation of the solvents, followed by flash chromatography (SiO2, hexane/AcOEt=3/7) and crystallization from AcOEt/heptane, yielded finally 0.015 g of the title compound as off-white solid.

Workup

dissolutionwas dissolved in 1.5 mL of abs
additionwas added
temperatureCooling
additionpouring
extractionice, twofold extraction with AcOEt
washwashing with water
dry with materialdrying over sodium sulfate, and evaporation of the solvents
customfollowed by flash chromatography (SiO2, hexane/AcOEt=3/7) and crystallization from AcOEt/heptane

Sources & evidence

ORD record: ord-2ab788bbff504d09a7bd4ac1d2ad2398
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163778B2

Reaction notes

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