1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 67376539, compound

HRID 1667205Notes

Reaction equation

HRID 1667205 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)[CH2:12][CH2:11][N:10]([CH2:13][C:14](O)=[O:15])[C:9]2=[O:17])=[CH:4][CH:3]=1.[Cl:25][C:26]1[CH:31]=[CH:30][C:29]([CH2:32][CH2:33]/[C:34](=[N:37]/[H])/[NH:35]O)=[CH:28][CH:27]=1.C(N=C=NCCCN(C)C)C>O1CCOCC1.C(OCC)(=O)C>[Cl:25][C:26]1[CH:27]=[CH:28][C:29]([CH2:32][CH2:33][C:34]2[N:35]=[C:14]([CH2:13][N:10]3[CH2:11][CH2:12][C:8]([C:18]4[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=4)([C:5]4[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=4)[C:9]3=[O:17])[O:15][N:37]=2)=[CH:30][CH:31]=1

Participants

6

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 673571912-(3,3-Bis(4-fluorophenyl)-2-oxopyrrolidin-1-yl)acetic acidHCID 178506470HCID 178506470, compound

Product 1

HCID 67376539HCID 67376539, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of the product of Example 58D (225 mg, 0.679 mmol) and the product of Example 165A (135 mg, 0.679 mmol) in 1,4-dioxane (4 mL) was added N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine (0.120 mL, 0.679 mmol) via syringe. The reaction was stirred at ambient temperature for 2.5 hours, then heated to 60° C. for 44 hours. The reaction was cooled to ambient temperature, diluted with ethyl acetate, and washed with 3 N aqueous HCl resulting in a homogeneous solution. Brine was added to force the phase separation. The organic layer was separated and washed with saturated aqueous NaHCO3 solution and brine, dried over Na2SO4, filtered, and concentrated in vacuo. Chromatography on silica gel (Analogix® Intelliflash™ 280; SF15-24 g column; 50% ethyl acetate/hexanes) yielded the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 7.36-7.27 (m, 4H), 7.27-7.21 (m, 2H), 7.15-7.07 (m, 2H), 7.07-6.96 (m, 4H), 4.79 (s, 2H), 3.46 (t, J=6.4, 2H), 3.00 (s, 4H), 2.80 (t, J=6.4, 2H); MS (ESI+) m/z 511 (M+NH4)+.

Workup

  1. temperatureheated to 60° C. for 44 hours
  2. temperatureThe reaction was cooled to ambient temperature
  3. washwashed with 3 N aqueous HCl resulting in a homogeneous solution
  4. additionBrine was added
  5. customthe phase separation
  6. customThe organic layer was separated
  7. washwashed with saturated aqueous NaHCO3 solution and brine
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c567ab8ce674446b9f6e7a3dd768e837
Source dataset
uspto-grants-2011_10
Patent number
US08044069B2

Reaction notes

Loading…