Morpholine → 8-Chloro-4-(3-{[3-(morpholin-4-ylcarbonyl)benzyl]oxy}phenyl)-3-phenylcinnoline

HRID 643329Notes

Reaction equation

C[Al](C)C.[NH:5]1[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1.C[O:12][C:13](=O)[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][O:21][C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([C:28]3[C:37]4[C:32](=[C:33]([Cl:38])[CH:34]=[CH:35][CH:36]=4)[N:31]=[N:30][C:29]=3[C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[CH:23]=2)[CH:15]=1>C1(C)C=CC=CC=1>[Cl:38][C:33]1[CH:34]=[CH:35][CH:36]=[C:37]2[C:32]=1[N:31]=[N:30][C:29]([C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1)=[C:28]2[C:24]1[CH:25]=[CH:26][CH:27]=[C:22]([O:21][CH2:20][C:16]2[CH:17]=[CH:18][CH:19]=[C:14]([C:13]([N:5]3[CH2:10][CH2:9][O:8][CH2:7][CH2:6]3)=[O:12])[CH:15]=2)[CH:23]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of trimethylaluminum (2 M solution in dichloromethane, 0.5 M) was added to a solution of morpholine (0.1 g) in 5 mL of toluene at room temperature. After 30 minutes 3-[3-(8-chloro-3-phenyl-cinnolin-4-yl)-phenoxymethyl]-benzoic acid methyl ester (50 mg) in 2 mL of toluene was added and the solution was heated to 60° C. for 15 hours. The reaction mixture was cooled to room temperature, quenched with diluted HCl and extracted with ethyl acetate. The combined organic extracts were washed with brine, dried (MgSO4), and concentrated in vacuo. The residue was purified by semi-preparative HPLC. MS (ES) m/z 536.2.

Workup

temperatureThe reaction mixture was cooled to room temperature
customquenched with diluted HCl
extractionextracted with ethyl acetate
washThe combined organic extracts were washed with brine
dry with materialdried (MgSO4)
concentrationconcentrated in vacuo
customThe residue was purified by semi-preparative HPLC

Sources & evidence

ORD record: ord-66ef48f8ae354f8c96e89b6d5357e27e
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07700595B2

Reaction notes

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