Methyl N-(triethylammoniosulfonyl)carbamate → 2-Ethyl-4-[5-(3-ethyl-5,5-dimethyl-4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-[1,3,4]oxadiazol-2-yl]-6-methyl-pyridine

HRID 2366131Notes

Reaction equation

[CH2:1]([C:3]1[CH:8]=[C:7]([C:9]([NH:11][NH:12][C:13]([C:15]2[S:16][C:17]([CH2:26][CH3:27])=[C:18]3[CH2:23][C:22]([CH3:25])([CH3:24])[CH2:21][CH2:20][C:19]=23)=O)=[O:10])[CH:6]=[C:5]([CH3:28])[N:4]=1)[CH3:2].CC[N+](S(N=C(OC)[O-])(=O)=O)(CC)CC>C1COCC1.CC(=O)OCC>[CH2:1]([C:3]1[CH:8]=[C:7]([C:9]2[O:10][C:13]([C:15]3[S:16][C:17]([CH2:26][CH3:27])=[C:18]4[CH2:23][C:22]([CH3:25])([CH3:24])[CH2:21][CH2:20][C:19]=34)=[N:12][N:11]=2)[CH:6]=[C:5]([CH3:28])[N:4]=1)[CH3:2]

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of crude 3-ethyl-5,5-dimethyl-4,5,6,7-tetrahydro-benzo[c]thiophene-1-carboxylic acid N′-(2-ethyl-6-methyl-pyridine-4-carbonyl)-hydrazide (289 mg, ca. 0.48 mmol) and Burgess Reagent (367 mg, 1.6 mmol) in THF (5 mL) is heated at 110° C. for 3 min in a microwave oven. The mixture is diluted with EA (50 mL) and extracted with 1M aq. NaOH (2×10 mL). The organic phase is dried (MgSO4), filtered and evaporated. The residue is purified by HPLC to give 2-ethyl-4-[5-(3-ethyl-5,5-dimethyl-4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-[1,3,4]oxadiazol-2-yl]-6-methyl-pyridine (53 mg); LC-MS: tR=0.96 min, [M+1]=382.26.

Workup

extractionextracted with 1M aq. NaOH (2×10 mL)
dry with materialThe organic phase is dried (MgSO4)
filtrationfiltered
customevaporated
customThe residue is purified by HPLC

Sources & evidence

ORD record: ord-6c8b432eef524e78964397a9c7918de7
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08697732B2

Reaction notes

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