1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → N-[cyclopropyl(phenyl)methyl]-2-(2-oxo-3,3-diphenylpyrrolidin-1-yl)acetamide

HRID 1667071Notes

Reaction equation

HRID 1667071 reaction equation
Cl.[CH:2]1([CH:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[NH2:6])[CH2:4][CH2:3]1.[O:13]=[C:14]1[C:18]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:17][CH2:16][N:15]1[CH2:31][C:32](O)=[O:33].C(N=C=NCCCN(C)C)C>ClCCl>[CH:2]1([CH:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[NH:6][C:32](=[O:33])[CH2:31][N:15]2[CH2:16][CH2:17][C:18]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:14]2=[O:13])[CH2:3][CH2:4]1

Participants

5

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 12280941Cyclopropyl(phenyl)methanamine hydrochlorideHCID 673590132-(2-Oxo-3,3-diphenylpyrrolidin-1-yl)acetic acid

Product 1

HCID 45275597N-[cyclopropyl(phenyl)methyl]-2-(2-oxo-3,3-diphenylpyrrolidin-1-yl)acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of cyclopropyl(phenyl)methanamine hydrogen chloride (0.050 g, 0.272 mmol), 2-(2-oxo-3,3-diphenylpyrrolidin-1-yl)acetic acid (Example 1C, 0.073 g, 0.247 mmol) and N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine (0.066 mL, 0.371 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 7.20-7.39 (m, 13H), 7.14-7.18 (m, 2H), 6.44 (d, J=8.1 Hz, 1H), 4.32 (t, J=8.6 Hz, 1H), 4.05 (d, J=15.3 Hz, 1H), 4.03 (d, J=15.6 Hz, 1H), 3.42-3.56 (m, 2H), 2.73-2.88 (m, 2H), 0.81-0.97 (m, 1H), 0.39-0.56 (m, 2H), 0.21-0.37 (m, 2H); MS (ESI−) m/z 423 (M−H)−.

Workup

  1. washthe title compound was eluted
  2. customover 20 minutes

Sources & evidence

ORD record
ord-7865526edd4a46a4841773f9974cbad4
Source dataset
uspto-grants-2011_10
Patent number
US08044069B2

Reaction notes

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