Triethylamine → HCID 42633472, compound

HRID 1009042Notes

Reaction equation

[CH3:1][C:2]1[CH:6]=[C:5]([S:7](=[O:10])(=[O:9])[NH2:8])[S:4][C:3]=1[CH2:11][CH2:12][O:13][C:14](=[O:16])[CH3:15].Cl[C:18](OC1C=CC=CC=1)=[O:19].C(N(CC)CC)C.[Br:34][C:35]1[S:39][C:38]([NH2:40])=[N:37][C:36]=1[CH3:41]>C(#N)C>[C:14]([O:13][CH2:12][CH2:11][C:3]1[S:4][C:5]([S:7]([NH:8][C:18](=[O:19])[NH:40][C:38]2[S:39][C:35]([Br:34])=[C:36]([CH3:41])[N:37]=2)(=[O:10])=[O:9])=[CH:6][C:2]=1[CH3:1])(=[O:16])[CH3:15]

Participants

Conditions

Temperature: 60 °C

Procedure

Acetic acid 2-(3-methyl-5-sulfamoyl-thiophen-2-yl)-ethyl ester (0.120 g, 0.456 mmol) was dissolved in 4.5 mL of abs. acetonitrile and treated successively with phenyl chloroformate (0.057 g, 1.00 eq.) and triethylamine (0.159 mL, 2.5 eq.), and the mixture kept at ambient temperature for 1 h. 5-Bromo-4-methyl-thiazol-2-ylamine (0.088 g, 1.00 eq.), dissolved in a tiny amount of acetonitrile, was then added, and the mixture heated to 60° C. over night. Cooling, pouring onto crashed ice/NH4Cl, twofold extraction with ethyl acetate, washing with brine, drying over sodium sulfate, and evaporation of the solvents, followed by flash chromatography (SiO2, ethyl acetate/5% MeOH), followed by crystallization from ethyl acetate/heptane, yielded finally 0.089 g of the title compound as light brown solid.

Workup

additionwas then added
temperatureCooling
additionpouring
extractionice/NH4Cl, twofold extraction with ethyl acetate
washwashing with brine
dry with materialdrying over sodium sulfate, and evaporation of the solvents
customfollowed by crystallization from ethyl acetate/heptane

Sources & evidence

ORD record: ord-8f8c23eb95994c4d97d81d5ba567246f
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07973051B2

Reaction notes

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