Dichloromethane → HCID 59540376, compound

HRID 923447Notes

Reaction equation

Br[CH2:2][C:3]1[CH:22]=[CH:21][C:6](/[CH:7]=[CH:8]/[C@@H:9]2[CH2:13][CH2:12][CH2:11][N:10]2[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[CH:5][CH:4]=1.[N+:23]([C:26]1[CH:39]=[CH:38][C:29]([CH2:30][NH:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[CH:28][CH:27]=1)([O-:25])=[O:24].C(=O)([O-])[O-].[K+].[K+].ClCCl>CN(C=O)C>[N+:23]([C:26]1[CH:27]=[CH:28][C:29]([CH2:30][N:31]([CH2:2][C:3]2[CH:22]=[CH:21][C:6](/[CH:7]=[CH:8]/[C@@H:9]3[CH2:13][CH2:12][CH2:11][N:10]3[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[CH:5][CH:4]=2)[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[CH:38][CH:39]=1)([O-:25])=[O:24]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of the product of Example 149D (1.09 g, 2.97 mmol) and N-(4-nitrobenzyl)aniline (0.677 g, 2.97 mmol) dissolved in DMF (10 mL) was added potassium carbonate (1.23 g, 8.9 mmol) and the mixture heated at 50° C. for 1 hour. After cooling, the solution had dichloromethane added to it and the mixture extracted with water. The organic extract was then dried, filtered, concentrated and purified by chromatography (silica gel, 0-2% methanol in dichloromethane) to afford 0.85 g (56%) of the title compound. MS (ESI) m/z 514 (M+H)+.

Workup

temperatureAfter cooling
additionadded to it
extractionthe mixture extracted with water
extractionThe organic extract
customwas then dried
filtrationfiltered
concentrationconcentrated
custompurified by chromatography (silica gel, 0-2% methanol in dichloromethane)

Sources & evidence

ORD record: ord-510f6c0c406144bea293de0a276194e4
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09278922B2

Reaction notes

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