Water → HCID 44472998, compound

HRID 2104800Notes

Reaction equation

Cl.[CH2:2]([NH2:4])[CH3:3].C[Al](C)C.[Cl:9][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]2[C:19]=1[N:18]=[CH:17][C:16]([CH3:20])=[C:15]2[C:21]1[CH:22]=[C:23]([CH:35]=[CH:36][CH:37]=1)[O:24][C:25]1[CH:26]=[C:27]([CH:32]=[CH:33][CH:34]=1)[C:28]([O:30]C)=O.O>C1(C)C=CC=CC=1>[Cl:9][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]2[C:19]=1[N:18]=[CH:17][C:16]([CH3:20])=[C:15]2[C:21]1[CH:22]=[C:23]([CH:35]=[CH:36][CH:37]=1)[O:24][C:25]1[CH:26]=[C:27]([CH:32]=[CH:33][CH:34]=1)[C:28]([NH:4][CH2:2][CH3:3])=[O:30]

Participants

Conditions

Temperature: 62.5 °C

Procedure

To a stirred suspension of ethylamine hydrochloride (41 mg, 0.50 mmol) in toluene (2 mL) at ambient temperature under nitrogen is added 2.0M trimethylaluminum in toluene (0.25 mL, 0.50 mmol). After 0.5 h, methyl 3-[3-(8-chloro-3-methylquinolin-4-yl)phenoxy]benzoate (101 mg, 0.25 mmol) is added and the reaction heated at 60-65° C. for 16 h. The cooled reaction is treated with water (2 mL), then 2M aq HCl (1 mL) and extracted with dichloromethane (2×5 mL). The combined extracts are dried (MgSO4), concentrated in vacuo, and the resulting oil is chromatographed on silica gel using 50:50, then 75:25 ethyl acetate:hexane as eluent. The title compound is isolated as a glass (Rf˜0.3 in first solvent system, 101 mg). MS (ES) m/z 417.2; HRMS: calcd for C25H21ClN2O2+H+, 417.13643; found (ESI, [M+H]+), 417.1357.

Workup

customThe cooled reaction
extraction2M aq HCl (1 mL) and extracted with dichloromethane (2×5 mL)
dry with materialThe combined extracts are dried (MgSO4)
concentrationconcentrated in vacuo
customthe resulting oil is chromatographed on silica gel using 50:50

Sources & evidence

ORD record: ord-df70d59e1d43423ebd7f55d9e4c5455b
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07576215B2

Reaction notes

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