1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 67443729, compound

HRID 1667217Notes

Reaction equation

HRID 1667217 reaction equation
[O:1]=[C:2]1[CH:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:6][CH2:5][CH2:4][N:3]1[CH2:14][C:15]([OH:17])=O.Br.[F:19][C:20]([F:31])([F:30])[C:21]1[CH:22]=[C:23]2[C:27](=[CH:28][CH:29]=1)[CH2:26][NH:25][CH2:24]2.C(N=C=NCCCN(C)C)C>ClCCl>[O:17]=[C:15]([N:25]1[CH2:24][C:23]2[C:27](=[CH:28][CH:29]=[C:21]([C:20]([F:19])([F:31])[F:30])[CH:22]=2)[CH2:26]1)[CH2:14][N:3]1[CH2:4][CH2:5][CH2:6][CH:7]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:2]1=[O:1]

Participants

5

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 673587022-(2-Oxo-3-phenylpiperidin-1-yl)acetic acidHCID 673590385-(Trifluoromethyl)isoindoline hydrobromide

Product 1

HCID 67443729HCID 67443729, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 2-(2-oxo-3-phenylpiperidin-1-yl)acetic acid (0.137 g, 0.587 mmol; Example 91D) and 5-(trifluoromethyl)isoindoline hydrogen bromide (0.173 g, 0.646 mmol) in dichloromethane (0.5 mL) was added N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine (0.156 mL, 0.881 mmol) and the reaction was stirred at room temperature overnight. The reaction was loaded directly onto a SF15-12 column (Analogix®) and the product eluted using a gradient of 50% ethyl acetate/hexanes to 100% ethyl acetate over 15 minutes (Flow=30 mL/minute) to provide the title compound. 1H NMR (300 MHz, CDCl3) δ 7.66-7.11 (m, 8H), 4.96 (s, 2H), 4.89 (s, 2H), 4.44 (dd, J=2.6, 15.6, 1H), 4.08 (dt, J=2.3, 6.8, 1H), 3.80-3.65 (m, 2H), 3.59 (dt, J=4.0, 5.6, 1H), 2.39-2.16 (m, 1H), 2.16-1.78 (m, 3H).

Workup

  1. washthe product eluted
  2. customover 15 minutes

Sources & evidence

ORD record
ord-4a854d3e9986493080a8c68d53783407
Source dataset
uspto-grants-2011_10
Patent number
US08044069B2

Reaction notes

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