1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 45274406, compound

HRID 1667260Notes

Reaction equation

HRID 1667260 reaction equation
[O:1]=[C:2]1[C:6]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH2:5][CH2:4][N:3]1[CH2:19][CH2:20][CH2:21][C:22](O)=[O:23].Br.[F:26][C:27]([F:38])([F:37])[C:28]1[CH:29]=[C:30]2[C:34](=[CH:35][CH:36]=1)[CH2:33][NH:32][CH2:31]2.C(N=C=NCCCN(C)C)C>ClCCl>[O:23]=[C:22]([N:32]1[CH2:31][C:30]2[C:34](=[CH:35][CH:36]=[C:28]([C:27]([F:26])([F:37])[F:38])[CH:29]=2)[CH2:33]1)[CH2:21][CH2:20][CH2:19][N:3]1[CH2:4][CH2:5][C:6]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:2]1=[O:1]

Participants

5

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 673590385-(Trifluoromethyl)isoindoline hydrobromideHCID 67360599HCID 67360599, compound

Product 1

HCID 45274406HCID 45274406, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 4-(2-oxo-3,3-diphenylpyrrolidin-1-yl)butanoic acid (Example 155A, 0.039 g, 0.121 mmol) and 5-(trifluoromethyl)isoindoline hydrobromide (0.036 g, 0.133 mmol) in dichloromethane (0.5 mL) was added N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine (0.032 mL, 0.181 mmol) and the reaction stirred for 18 hours. The reaction was loaded onto a GraceResolv™ 4 g silica gel column (Grace Davison Discovery Sciences) and the product eluted with a gradient of 5% ethyl acetate/hexanes to 100% ethyl acetate/hexanes (Flow=20 mL/minute) over 30 minutes to give the title compound. 1H NMR (300 MHz, CDCl3) δ 7.55 (d, J=8.0, 1H), 7.45 (d, J=14.3, 1H), 7.36-7.13 (m, 11H), 4.67 (d, J=9.6, 2H), 4.57 (d, J=5.5, 2H), 3.50 (t, J=6.5, 2H), 3.41 (t, J=6.5, 2H), 2.74 (t, J=6.5, 2H), 2.26 (t, J=6.9, 2H), 2.01 (p, J=6.6, 2H); MS (ESI+) m/z 493.1 (M+H)+.

Workup

  1. washthe product eluted with a gradient of 5% ethyl acetate/hexanes to 100% ethyl acetate/hexanes (Flow=20 mL/minute) over 30 minutes

Sources & evidence

ORD record
ord-bc2d6159bbbd444cbc9749d9dba4ac30
Source dataset
uspto-grants-2011_10
Patent number
US08044069B2

Reaction notes

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