Water → HCID 58913086, compound

HRID 1296683Notes

Reaction equation

[OH:1][C:2]1[CH:32]=[CH:31][C:5]([CH2:6][C:7]2[C:16]3[C:11](=[CH:12][C:13]([O:18][CH3:19])=[C:14]([CH3:17])[CH:15]=3)[O:10][C:9](=[O:20])[C:8]=2[C:21]2[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=2)=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH2:39]1[CH2:43][N:42]([CH2:44][CH2:45]Cl)[CH2:41][CH2:40]1.Cl.O>CCO.C(Cl)Cl.O>[CH3:19][O:18][C:13]1[CH:12]=[C:11]2[C:16]([C:7]([CH2:6][C:5]3[CH:31]=[CH:32][C:2]([O:1][CH2:45][CH2:44][N:42]4[CH2:43][CH2:39][CH2:40][CH2:41]4)=[CH:3][CH:4]=3)=[C:8]([C:21]3[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:28])[F:29])=[CH:23][CH:22]=3)[C:9](=[O:20])[O:10]2)=[CH:15][C:14]=1[CH3:17]

Participants

Conditions

Temperature: 55 °C

Procedure

A mixture of 4-(4-hydroxybenzyl)-7-methoxy-6-methyl-3-(4-trifluoromethyl-phenyl)-chromen-2-one (50 mg, 0.113 mmol), K2CO3 (48 mg, 0.35 mmol) and 1-(2-chloroethyl)pyrrolidine.HCl (24 mg, 0.14 mmol) in EtOH (1 mL) containing water (100 μL) was stirred at 55° C. for 5 h. The mixture was cooled to room temperature and was poured into CH2Cl2—H2O. The layers were separated and the aqueous phase was extracted with CH2Cl2 (3×). The combined organic layers were dried (MgSO4) and the solvent was removed in vacuo. The residue was purified using flash chromatography (silica gel, 40:1 CH2Cl2:MeOH) to provide the title compound as a beige solid (37 mg, 61%). MS (ESI) m/z 537.9 (M+H)+; HPLC tR 5.22 min.

Workup

temperatureThe mixture was cooled to room temperature
customThe layers were separated
extractionthe aqueous phase was extracted with CH2Cl2 (3×)
dry with materialThe combined organic layers were dried (MgSO4)
customthe solvent was removed in vacuo
customThe residue was purified

Sources & evidence

ORD record: ord-ebd2e3c50f924059b9f3e1c094a6c832
Source dataset: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07247646B2

Reaction notes

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