Triphenylphosphine → 6-(2-morpholine-4-ylethoxy)-1-oxo-3-pheny-1H-indene-2-carboxylic acid cyclohexylamide

HRID 19556

Reaction equation

[CH:1]1([NH:7][C:8]([C:10]2[C:11](=[O:26])[C:12]3[C:17]([C:18]=2[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:16][CH:15]=[C:14]([OH:25])[CH:13]=3)=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.O[CH2:28][CH2:29][N:30]1[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCCC1.C1C=CC=CC=1>[CH:1]1([NH:7][C:8]([C:10]2[C:11](=[O:26])[C:12]3[C:17]([C:18]=2[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[CH:16][CH:15]=[C:14]([O:25][CH2:28][CH2:29][N:30]2[CH2:35][CH2:34][O:33][CH2:32][CH2:31]2)[CH:13]=3)=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

Conditions

Temperature: 0 °C

Procedure

6-Hydroxy-1-oxo-3-phenyl-1H-indene-2-carboxylic acid cyclohexylamide (141 mg, 0.41 mmol) obtained in Step 3 was dissolved in tetrahydropyran/benzene (3 mL/2 mL), and 4-(2-hydroxyethyl)morpholine (99 μl, 0.82 mmol) and triphenylphosphine (215 mg, 0.82 mmol) were added thereto. Then, diisopropyl azodicarboxilate (149 μl, 0.82 mmol) was added slowly thereto at 0° C., and stirred for 2 hrs at RT. The resulting mixture washed with saturated saline and extracted with ethyl acetate. The organic layer was separated, dried over anhydrous MgSO4 and concentrated under a reduced pressure. The resulting residue was purified by flash chromatography to obtain 165 mg of the titled compound (yield: 88.3%).

Workup

washThe resulting mixture washed with saturated saline
extractionextracted with ethyl acetate
customThe organic layer was separated
dry with materialdried over anhydrous MgSO4
concentrationconcentrated under a reduced pressure
customThe resulting residue was purified by flash chromatography

Sources & evidence

ORD record: ord-e8d480256d7b46968a7d67c25afe805a
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07745439B2

Linked notes

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