Potassium Carbonate → HCID 58046659, compound

HRID 2362966Notes

Reaction equation

[O:1]=[C:2]1[C:6]2([CH2:11][CH2:10][NH:9][CH2:8][CH2:7]2)[N:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:4][N:3]1[CH2:18][C:19]1[CH:20]=[C:21]([CH:29]=[CH:30][CH:31]=1)[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23].I[CH2:33][CH2:34][CH2:35][C:36]([C:38]1[CH:43]=[CH:42][C:41]([O:44][CH3:45])=[CH:40][CH:39]=1)=[O:37].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:45][O:44][C:41]1[CH:42]=[CH:43][C:38]([C:36](=[O:37])[CH2:35][CH2:34][CH2:33][N:9]2[CH2:10][CH2:11][C:6]3([N:5]([C:12]4[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=4)[CH2:4][N:3]([CH2:18][C:19]4[CH:20]=[C:21]([CH:29]=[CH:30][CH:31]=4)[C:22]([O:24][C:25]([CH3:28])([CH3:26])[CH3:27])=[O:23])[C:2]3=[O:1])[CH2:7][CH2:8]2)=[CH:39][CH:40]=1

Participants

Conditions

Temperature: 68 °C

Procedure

A mixture of tert-butyl 3-((4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoate (300 mg, 0.71 mmol, 1 equiv), 4-iodo-1-(4-methoxyphenyl)butan-1-one (216.5 mg, 0.71 mmol, 1 equiv), and potassium carbonate (285.2 mg, 2.136 mmol, 3 equiv) in N,N-dimethylformamide was stirred at 68° C. for 16 h. After cooling the reaction mixture, the crude mixture was partitioned between ethyl acetate and water. The organic layer was dried over MgSO4, filtered, concentrated, and the crude residue was purified using the Biotage flash chromatography system (SNAP 10 g cartridge, Rf=0.4, gradient—1%-8% methanol in dichloromethane) to afford the title compound as an oil (100 mg, 25%); MS for C36H43N3O5 m/z 598.3 (M+H)+.

Workup

temperatureAfter cooling the reaction mixture
customthe crude mixture was partitioned between ethyl acetate and water
dry with materialThe organic layer was dried over MgSO4
filtrationfiltered
concentrationconcentrated
customthe crude residue was purified

Sources & evidence

ORD record: ord-98e541a25dd7443696dd72ee653362ba
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08691836B2

Reaction notes

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