Triethylamine → HCID 67273738, compound

HRID 1696752Notes

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.[C:32]([Si:36]([CH3:51])([CH3:50])[O:37][CH2:38][CH2:39][NH:40][C:41]1[CH:46]=[C:45]([S:47][CH3:48])[CH:44]=[C:43]([NH2:49])[N:42]=1)([CH3:35])([CH3:34])[CH3:33]>C(#N)C>[C:32]([Si:36]([CH3:51])([CH3:50])[O:37][CH2:38][CH2:39][NH:40][C:41]1[N:42]=[C:43]([NH:49][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])[CH:44]=[C:45]([S:47][CH3:48])[CH:46]=1)([CH3:35])([CH3:34])[CH3:33]

Participants

Conditions

Temperature: 60 °C

Procedure

5-(2-Methoxy-ethyl)-4-methyl-thiophene-2-sulfonic acid amide (0.082 g, 0.48 mmol) was dissolved in 2.8 mL of abs. acetonitrile and treated successively with phenyl chloroformate (0.075 g, 1.0 eq.) and triethylamine (0.167 mL, 2.5 eq.), and the mixture kept at ambient temperature for 1 h. The above prepared N-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-methylsulfanyl-pyridine-2,6-diamine (0.150 g, 1.0 eq.), dissolved in a tiny amount of acetonitrile, was then added, and the mixture heated to 60° C. for 18 h. Cooling, pouring onto crashed ice, twofold extraction with AcOEt, washing with brine, drying over magnesium sulfate, and evaporation of the solvents, followed by flash chromatography (SiO2, hexane/AcOEt=1/1), yielded eventually 0.161 g of the title compound as off-white foam.

Workup

additionwas then added
temperatureCooling
additionpouring
extractionice, twofold extraction with AcOEt
washwashing with brine
dry with materialdrying over magnesium sulfate, and evaporation of the solvents

Sources & evidence

ORD record: ord-dc30795d521243829173aef86531e5bc
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163778B2

Reaction notes

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