Potassium Carbonate → HCID 67086542, compound

HRID 2174978Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:14][CH:13]2[CH:9]1[CH2:10][NH:11][CH2:12]2)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl[C:16]1[CH:25]=[N:24][C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[N:17]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[C:1]([O:5][C:6]([N:8]1[CH2:14][CH:13]2[CH:9]1[CH2:10][N:11]([C:16]1[CH:25]=[N:24][C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[N:17]=1)[CH2:12]2)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 80 °C

Procedure

Intermediate 2 (0.51 mmol), 2-chloro-quinoxaline (0.51 mmol) and K2CO3 (1.53 mmol) were taken up in DMF (0.2 M). The mixture heated to 80° C. and allowed to heat at 80° C. overnight. The mixture was cooled to room temperature, diluted with water, and extracted with diethyl ether (3×100 mL). The organics were combined, dried over MgSO4, filtered, and concentrated. The resulting crude product was purified by flash column chromatography (FCC) (50-100% EtOAc/hex) to provide 3-quinoxalin-2-yl-3,6-diaza-bicyclo[3.2.0]heptane-6-carboxylic acid tert-butyl ester (84%). MS (ESI) mass calcd. for C18H22N4O2, 326.39; m/z found, 327.2 [M+H]+. 1H NMR (400 MHz, CDCl3): 8.48 (s, 1H), 7.93-7.87 (m, 1H), 7.76-7.69 (m, 1H), 7.62-7.55 (m, 1H), 7.45-7.36 (m, 1H), 4.90 (br s, 1H), 4.41 (br s, 1H), 4.27-4.09 (m, 2H), 3.68-3.61 (m, 1H), 3.49-3.41 (m, 1H), 3.34-3.20 (m, 2H), 1.45 (br s, 9H).

Workup

temperatureto heat at 80° C. overnight
temperatureThe mixture was cooled to room temperature
extractionextracted with diethyl ether (3×100 mL)
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated
customThe resulting crude product was purified by flash column chromatography (FCC) (50-100% EtOAc/hex)

Sources & evidence

ORD record: ord-7c39b77cc08c45bcb8a67c05cb61c42d
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09062044B2

Reaction notes

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