Ethyl diazoacetate → HCID 46200652, compound

HRID 1959447Notes

Reaction equation

[C:1]1([C:7]2[O:11][C:10]([C:12]3[C:13]([NH2:20])=[N:14][CH:15]=[C:16]([CH:18]=[CH2:19])[N:17]=3)=[N:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N+](=[CH:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])=[N-]>C1(C)C=CC=CC=1>[NH2:20][C:13]1[N:14]=[CH:15][C:16]([CH:18]2[CH2:19][CH:23]2[C:24]([O:26][CH2:27][CH3:28])=[O:25])=[N:17][C:12]=1[C:10]1[O:11][C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[N:8][N:9]=1

Participants

Conditions

Temperature: 110 °C

Procedure

To a vial charged with 3-(5-phenyl-1,3,4-oxadiazol-2-yl)-5-vinyl-pyrazin-2-amine (26 mg, 0.01 mmol) under an atmosphere of nitrogen at room temperature was slowly added a solution of ethyl 2-diazoacetate (34 mg, 31 μL, 0.1 mmol) in toluene (350 μL) over a period of 10 min. The reaction mixture was heated at 110° C. for 1 h. The reaction mixture was cooled to room temperature and the solvent was removed under reduced pressure. The crude material was dissolved in DMSO (1 mL), filtered and purified via reverse phase column chromatography using 10 to 99% MeOH—H2O (TFA modifier) to obtain ethyl 2-[5-amino-6-(5-phenyl-1,3,4-oxadiazol-2-yl)pyrazin-2-yl]cyclopropanecarboxylate. 1H NMR (400.0 MHz, CDCl3) δ 8.23-8.15 (m, 3H), 7.59-7.50 (m, 3H), 4.19 (q, J=7.1 Hz, 2H), 2.64 (dd, J=6.2, 12.7 Hz, 1H), 2.25 (dd, J=5.5, 12.4 Hz, 1H), 1.66-1.61 (m, 2H) and 1.39-1.24 (m, 3H) ppm; LC/MS m/z 352.2 [M+H]+.

Workup

temperatureThe reaction mixture was cooled to room temperature
customthe solvent was removed under reduced pressure
dissolutionThe crude material was dissolved in DMSO (1 mL)
filtrationfiltered
custompurified via reverse phase column chromatography

Sources & evidence

ORD record: ord-4ab0a821d7b6448fb95c1997e07679af
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08410112B2

Reaction notes

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