N,N'-Dimethylethylenediamine → HCID 58305379, compound

HRID 1805354Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([N:11]2[C:19]3[C:14](=[CH:15][C:16]([F:20])=[CH:17][CH:18]=3)[C@@:13]3([CH2:22][C@@:21]3([C:26]3[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=3)[CH:23]([CH3:25])[CH3:24])[C:12]2=[O:33])[CH:10]=1)[C:5]([O-:7])=[O:6].BrC1C=C([CH:41]=[C:42]([N:44]2C3C(=CC(F)=CC=3)[C@]3(C[C@]3(C3C=CC(Cl)=CC=3)C(C)C)C2=O)C=1)C([O-])=O.O1CC(=O)N=[C-:68]1.[C:73]([O-:76])([O-])=[O:74].[K+].[K+].CNCCNC>C(#N)C.[Cu]I>[CH3:68][O:7][C:5](=[O:6])[C:4]1[CH:3]=[C:2]([N:44]2[CH2:42][CH2:41][O:76][C:73]2=[O:74])[CH:10]=[C:9]([N:11]2[C:19]3[C:14](=[CH:15][C:16]([F:20])=[CH:17][CH:18]=3)[C@@:13]3([CH2:22][C@@:21]3([C:26]3[CH:27]=[CH:28][C:29]([Cl:32])=[CH:30][CH:31]=3)[CH:23]([CH3:25])[CH3:24])[C:12]2=[O:33])[CH:8]=1

Participants

Conditions

Temperature: 80 °C

Procedure

3-bromo-5-((1S,2S)-2-(4-chlorophenyl)-5′-fluoro-2-isopropyl-2′-oxospiro[cyclopropane-1,3′-indoline]-1′-yl)benzoate, 3-bromo-5-((1R,2R)-2-(4-chlorophenyl)-5′-fluoro-2-isopropyl-2′-oxospiro[cyclopropane-1,3′-indoline]-1′-yl)benzoate (0.545 g, 1 mmol), 2-oxazolidone (0.105 g, 1.2 mmol), CuI (20 mg), and K2CO3 (0.276 g, 2 mmol) were placed in a Schlenk tube under Argon atmosphere and dissolved in dry acetonitrile. The N,N′-dimethyl-1,2-ethanediamine (21 μL, 20% equiv) was added into the mixture. The mixture was stirred at 80° C. for 14 hours. The solvent was removed in vacuo and the residue was purified by flash column chromatography to give the title compound as white powder (0.40 g, 73%). LC/MS m/e calcd. for C30H26ClFN2O5: 548, observed (M+H)+: 549.5

Workup

customThe solvent was removed in vacuo
customthe residue was purified by flash column chromatography

Sources & evidence

ORD record: ord-3170985e8f874739914a5ff4fcaf0e4c
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08354443B2

Reaction notes

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