Potassium Carbonate → HCID 71116084, compound

HRID 1423842Notes

Reaction equation

[NH2:1][CH2:2][C:3]1([CH3:19])[CH2:18][CH2:17][CH2:16][C:5]2([O:9][C:8](=[O:10])[N:7]([CH2:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH2:6]2)[CH2:4]1.[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[C:23](F)[CH:22]=1.C(=O)([O-])[O-].[K+].[K+]>CC#N>[Cl:20][C:21]1[CH:22]=[CH:23][C:24]([N+:27]([O-:29])=[O:28])=[C:25]([NH:1][CH2:2][C:3]2([CH3:19])[CH2:18][CH2:17][CH2:16][C:5]3([O:9][C:8](=[O:10])[N:7]([CH2:11][C:12]([CH3:14])([CH3:15])[CH3:13])[CH2:6]3)[CH2:4]2)[CH:26]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A solution containing 7-(aminomethyl)-7-methyl-3-neopentyl-1-oxa-3-azaspiro[4.5]decan-2-one (0.100 g, 0.373 mmol) in MeCN (5 mL) was treated with 4-chloro-2-fluoro-nitrobenzene (0.065 g, 0.373 mmol) and potassium carbonate (0.077 g, 0.559 mmol). The reaction mixture was heated to 50° C. and stirred for 18 h. Additional 4-chloro-2-fluoro-nitrobenzene (0.020 g, 0.114 mmol) was added, and the reaction was stirred at 50° C. for an additional 3 h. The reaction was cooled to rt and concentrated for purification on a 40 g silica gel column (0-100% EtOAc/hexanes, 25 min gradient; 40 mL/min elution; 254 nm detection) to afford the title compound (0.175 g, 100% yield). MS (m/z) 424.1 (M+H+).

Workup

stirringthe reaction was stirred at 50° C. for an additional 3 h
temperatureThe reaction was cooled to rt
concentrationconcentrated for purification on a 40 g silica gel column (0-100% EtOAc/hexanes, 25 min gradient; 40 mL/min elution; 254 nm detection)

Sources & evidence

ORD record: ord-dcf5af00944c486ea985709fb7f93dad
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08927585B2

Reaction notes

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