Cyclopropanecarbonyl chloride → HCID 118079498, compound

HRID 1485742Notes

Reaction equation

C(N(CC)C(C)C)(C)C.[Br:10][C:11]1[CH:20]=[C:19]2[C:14]([NH:15][C@@H:16]([CH3:30])[CH2:17][N:18]2[C:21]2[O:22][C:23]3[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=3[N:25]=2)=[CH:13][CH:12]=1.[CH:31]1([C:34](Cl)=[O:35])[CH2:33][CH2:32]1>ClCCCl>[O:22]1[C:23]2[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=2[N:25]=[C:21]1[N:18]1[C:19]2[C:14](=[CH:13][CH:12]=[C:11]([Br:10])[CH:20]=2)[N:15]([C:34]([CH:31]2[CH2:33][CH2:32]2)=[O:35])[C@@H:16]([CH3:30])[CH2:17]1

Participants

Conditions

Temperature: 50 °C

Procedure

N,N-Diisopropylethylamine (0.041 mL, 0.232 mmol) was added to a solution of (S)-2-(7-bromo-3-methyl-3,4-dihydroquinoxaline-1(2H)-yl)benzo[d]oxazole (0.016 g, 0.046 mmol) and cyclopropanecarbonyl chloride (0.021 mL, 0.232 mmol) in 1,2-dichloroethane (1.0 mL), and the mixture stirred at 50° C. for 2.5 h. The reaction mixture was partitioned between water and dichloromethane. The aqueous phase was separated and extracted with dichloromethane. The combined organic phases were washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated to afford (S)-(4-(benzo[d]oxazol-2-yl)-6-bromo-2-methyl-3,4-dihydroquinoxaline-1(2H)-yl)(cyclopropyl)methanone (0.019 g, 99%) as a brown oil. MS (ESI, pos. ion) m/z 412, 414 [M+H]+.

Workup

customThe reaction mixture was partitioned between water and dichloromethane
customThe aqueous phase was separated
extractionextracted with dichloromethane
washThe combined organic phases were washed with brine
dry with materialdried over anhydrous sodium sulfate
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-64407ede47e24d06b4bf936d7eb98ee7
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09422281B2

Reaction notes

Loading…