Methyl 4-(2-(4-fluoro-2-methoxyphenoxy)phenylcarbamoyl)benzoate → HCID 59783633, compound

HRID 1946586Notes

Reaction equation

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

Participants

Conditions

Temperature: 130 °C

Procedure

A stirring mixture of title compound 92 (2 g, 5.06 mmol) in polyphosphoric acid (4.76 ml, 41.7 mmol) was heated at 130° C. for 3 h. The reaction mixture was cooled, diluted with dichloromethane and water and stirred overnight. The layers were separated and the aqueous layer was extracted with dichloromethane. The combined organic layers were washed with brine, dried over MgSO4, filtered and solvent evaporated. The crude residue was purified via ISCO (0-25% Hex/EtOAc; 40 g silica gel column) to afford title compound 93 (125 mg, 6.5%) as a light yellow solid. LRMS (ESI): (calc) 377.11 (found) 378.4 (MH)+.

Workup

temperatureThe reaction mixture was cooled
customThe layers were separated
extractionthe aqueous layer was extracted with dichloromethane
washThe combined organic layers were washed with brine
dry with materialdried over MgSO4
filtrationfiltered
customsolvent evaporated
customThe crude residue was purified via ISCO (0-25% Hex/EtOAc; 40 g silica gel column)

Sources & evidence

ORD record: ord-b940df8c8cab43efbaab1e42cb6fb451
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08399452B2

Reaction notes

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