Methyl N-(triethylammoniosulfonyl)carbamate → 2-Ethyl-6-methyl-4-[5-((1as,5ar)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-[1,3,4]oxadiazol-2-yl]-pyridine

HRID 1924831Notes

Reaction equation

[CH3:1][C:2]1([CH3:27])[CH:4]2[CH2:5][C:6]3[C:10]([CH:3]12)=[C:9]([CH3:11])[S:8][C:7]=3[C:12]([NH:14][NH:15][C:16](=O)[C:17]1[CH:22]=[C:21]([CH3:23])[N:20]=[C:19]([CH2:24][CH3:25])[CH:18]=1)=[O:13].CC[N+](S(N=C(OC)[O-])(=O)=O)(CC)CC>C1COCC1.CC(=O)OCC>[CH2:24]([C:19]1[CH:18]=[C:17]([C:16]2[O:13][C:12]([C:7]3[S:8][C:9]([CH3:11])=[C:10]4[C:6]=3[CH2:5][C@H:4]3[C:2]([CH3:27])([CH3:1])[C@H:3]34)=[N:14][N:15]=2)[CH:22]=[C:21]([CH3:23])[N:20]=1)[CH3:25]

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of crude 2-ethyl-6-methyl-isonicotinic acid N′-(1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalene-4-carbonyl)-hydrazide (350 mg, ca. 0.5 mmol) and Burgess Reagent (385 mg, 1.62 mmol) in THF (5 mL) is heated at 110° C. for 3 min in a microwave oven. The mixture is diluted with EA (10 mL) and extracted with sat. aq. Na2CO3 (2×5 mL). The organic phase is dried (Na2SO4), filtered and evaporated to give crude product (50.9 mg) that is purified by HPLC to give 2-ethyl-6-methyl-4-[5-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-[1,3,4]oxadiazol-2-yl]-pyridine (16 mg) as a light yellow powder; LC-MS: tR=0.91 min, [M+1]=366.21.

Workup

extractionextracted with sat. aq. Na2CO3 (2×5 mL)
dry with materialThe organic phase is dried (Na2SO4)
filtrationfiltered
customevaporated
customto give crude product (50.9 mg) that
customis purified by HPLC

Sources & evidence

ORD record: ord-e1f6669b43c94f878cb39232ff735f39
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08178562B2

Reaction notes

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