1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 67359332, compound

HRID 1667107Notes

Reaction equation

HRID 1667107 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]([OH:33])=O.Cl.Cl.[F:36][C:37]([F:53])([F:52])[C:38]1[CH:39]=[C:40]([CH:44]([N:46]2[CH2:51][CH2:50][NH:49][CH2:48][CH2:47]2)[CH3:45])[CH:41]=[CH:42][CH:43]=1>ClCCl>[O:33]=[C:31]([N:49]1[CH2:48][CH2:47][N:46]([CH:44]([C:40]2[CH:41]=[CH:42][CH:43]=[C:38]([C:37]([F:52])([F:53])[F:36])[CH:39]=2)[CH3:45])[CH2:51][CH2:50]1)[CH2:30][N:14]1[CH2:15][CH2:16][C:17]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:13]1=[O:12]

Participants

5

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 67358282HCID 67358282, compoundHCID 673590132-(2-Oxo-3,3-diphenylpyrrolidin-1-yl)acetic acid

Product 1

HCID 67359332HCID 67359332, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine (0.074 mL, 0.416 mmol), 2-(2-oxo-3,3-diphenylpyrrolidin-1-yl)acetic acid (Example 1C, 0.058 g, 0.198 mmol) and the product from Example 44B (0.066 g, 0.198 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 7.40-7.56 (m, 4H), 7.20-7.37 (m, 10H), 4.10-4.22 (m, 2H), 3.52-3.63 (m, 2H), 3.50 (t, J=6.6 Hz, 2H), 3.34-3.43 (m, 3H), 2.80 (t, J=6.5 Hz, 2H), 2.43-2.51 (m, 1H), 2.16-2.36 (m, 3H), 1.33 (d, J=6.7 Hz, 3H); MS (ESI+) m/z 536 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-b3ab4141447548058bd174aa6d66aa0f
Source dataset
uspto-grants-2011_10
Patent number
US08044069B2

Reaction notes

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