1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 1-[2-(5-fluoro-1,3-dihydro-2H-isoindol-2-yl)-2-oxoethyl]-3,3-diphenylpyrrolidin-2-one
Reaction equation
C(N=C=NCCCN(C)C)C.[O:12]=[C:13]1[C:17]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:16][CH2:15][N:14]1[CH2:30][C:31](O)=[O:32].Cl.[F:35][C:36]1[CH:37]=[C:38]2[C:42](=[CH:43][CH:44]=1)[CH2:41][NH:40][CH2:39]2>ClCCl>[F:35][C:36]1[CH:37]=[C:38]2[C:42](=[CH:43][CH:44]=1)[CH2:41][N:40]([C:31](=[O:32])[CH2:30][N:14]1[CH2:15][CH2:16][C:17]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:13]1=[O:12])[CH2:39]2Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine (0.067 mL, 0.381 mmol), 2-(2-oxo-3,3-diphenylpyrrolidin-1-yl)acetic acid (Example 1C, 0.075 g, 0.254 mmol) and 5-fluoroisoindoline hydrochloride (0.044 g, 0.254 mmol) in dichloromethane (0.5 mL) was stirred at room temperature. After stirring overnight, the reaction was loaded directly onto a SF15-12 silica gel column (Analogix®, Burlington, Wis.), and the title compound was eluted using a gradient of 5% to 100% ethyl acetate/hexanes over 20 minutes (flow=30 mL/minute). 1H NMR (300 MHz, CDCl3) δ ppm 7.13-7.40 (m, 11H), 6.88-7.05 (m, 2H), 4.75-4.81 (m, 4H), 4.23 (s, 2H), 3.60 (t, J=6.6 Hz, 2H), 2.85 (t, J=6.6 Hz, 2H); MS (ESI+) m/z 415 (M+H)+.
Workup
- washthe title compound was eluted
- customover 20 minutes
Sources & evidence
- ORD record
- ord-e7f4fecde14b47d8815b0d5f8fcce467
- Source dataset
- uspto-grants-2011_10
- Patent number
- US08044069B2
Reaction notes
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