Triethylamine → HCID 42633832, compound

HRID 1009056Notes

Reaction equation

[CH3:1][O:2][CH2:3][CH2:4][C:5]1[S:9][C:8]([S:10]([NH2:13])(=[O:12])=[O:11])=[CH:7][C:6]=1[CH3:14].Cl[C:16](OC1C=CC=CC=1)=[O:17].C(N(CC)CC)C.[CH2:32]([C:34]1[N:35]=[C:36]([NH2:41])[S:37][C:38]=1[S:39][CH3:40])[CH3:33]>C(#N)C>[CH2:32]([C:34]1[N:35]=[C:36]([NH:41][C:16]([NH:13][S:10]([C:8]2[S:9][C:5]([CH2:4][CH2:3][O:2][CH3:1])=[C:6]([CH3:14])[CH:7]=2)(=[O:12])=[O:11])=[O:17])[S:37][C:38]=1[S:39][CH3:40])[CH3:33]

Participants

Conditions

Temperature: 60 °C

Procedure

5-(2-Methoxy-ethyl)-4-methyl-thiophene-2-sulfonic acid amide (0.235 g, 1.00 mmol) was dissolved in 6 mL of abs. acetonitrile and treated successively with phenyl chloroformate (0.157 g, 1.00 eq.) and triethylamine (0.348 mL, 2.5 eq.), and the mixture kept at ambient temperature for 1. h. The above prepared 4-ethyl-5-methylsulfanyl-thiazol-2-ylamine (0.211 g, 1.00 eq. as hydrochloride) was then added, and the mixture heated to 60° C. over night. Cooling, pouring onto crashed ice, twofold extraction with ethyl acetate, washing with brine, drying over sodium sulfate, and evaporation of the solvents, followed by flash chromatography (SiO2, ethyl acetate/MeOH=95/5) and trituration over heptane yielded 0.296 g of the title compound as light brown solid.

Workup

customkept at ambient temperature for 1
additionwas then added
temperatureCooling
additionpouring
extractionice, twofold extraction with ethyl acetate
washwashing with brine
dry with materialdrying over sodium sulfate, and evaporation of the solvents

Sources & evidence

ORD record: ord-119f63ccebb6416d9dc9da17a48aedd5
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07973051B2

Reaction notes

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