Diisopropylethylamine → HCID 59850171, compound

HRID 2064178Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of 4-fluoro-2-methyl-5-nitrophenyl 1-methylethyl ether (D73) (0.53 mmol, 115 mg) in dimethylformamide (3 mL) was treated with 1,1-dimethylethyl 4-amino-1-piperidinecarboxylate (0.53 mmol, 106 mg, 1 eq) and diisopropylethylamine (0.53 mmol, 68.5 mg, 1 eq) under argon at room temperature and then heated at 80° C. overnight. The mixture was then concentrated under reduced pressure, then treated with 10% aqueous sodium carbonate solution and extracted with ether/ethyl acetate. The organics were dried, concentrated under reduced pressure and purified by chromatography on silica (ethyl acetate/petrol ether) to give the title compound as a solid (0.2 mmol, 80 mg, 39% yield). M+H 338.1 for main fragment (loss of tert-butyl group).

Workup

concentrationThe mixture was then concentrated under reduced pressure
additiontreated with 10% aqueous sodium carbonate solution
extractionextracted with ether/ethyl acetate
customThe organics were dried
concentrationconcentrated under reduced pressure
custompurified by chromatography on silica (ethyl acetate/petrol ether)

Sources & evidence

ORD record: ord-241cca5c6c944b57ba9bd69e565b1830
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08288412B2

Reaction notes

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