1,2-Dichloroethane → HCID 68872204, compound

HRID 1986362Notes

Reaction equation

HRID 1986362 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][C:12]([NH:18][C:19]3[C:24]([NH2:25])=[CH:23][N:22]=[C:21]([O:26][C:27]4[CH:32]=[CH:31][CH:30]=[C:29]([NH:33][C:34](=[O:36])[CH3:35])[CH:28]=4)[CH:20]=3)=[CH:13][CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:37]([CH2:39][C:40](O)=O)#[N:38].C(Cl)CCl.CN1CCC(=C2C3C(=CC=CC=3)C=CC3C2=CC=CC=3)CC1>CN(C=O)C.CC(O)=O.O.CCN(CC)CC>[C:1]([O:5][C:6]([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][C:12]([N:18]3[C:19]4[CH:20]=[C:21]([O:26][C:27]5[CH:32]=[CH:31][CH:30]=[C:29]([NH:33][C:34](=[O:36])[CH3:35])[CH:28]=5)[N:22]=[CH:23][C:24]=4[N:25]=[C:40]3[CH2:39][C:37]#[N:38])=[CH:13][CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

9

Reactant 4

HCID 111,2-DichloroethaneHCID 2913CyproheptadineHCID 9740Cyanoacetic acidHCID 68875465HCID 68875465, compound

Product 1

HCID 68872204HCID 68872204, compound

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

The product from Step 3 (2.54 g crude) and cyanoacetic acid (0.88 g, 10.4 mmol) were dissolved in DMF (10 mL) and Et3N (3.6 mL) was added. To the solution was added EDC (2.2 g, 11.4 mmol), and the mixture was allowed to stir at rt for 2 days. The reactin mixture was poured into water and extracted with ethyl acetate. The separated organic layer was dried over MgSO4, filtered, and concentrated to give a dark oil. The oil was dissolved in AcOH (5 mL) and the solution was heated at 100° C. for 4 hours then cooled and concentrated in-vacuo to give the title compound as a dark foam that was taken on without further purification. MS (ES+) m/e 540 [M+H]+.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe separated organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give a dark oil
  6. temperaturethe solution was heated at 100° C. for 4 hours
  7. temperaturethen cooled
  8. concentrationconcentrated in-vacuo

Sources & evidence

ORD record
ord-525188c6465448da8fdc69741a6f1dbf
Source dataset
uspto-grants-2009_06
Patent number
US07547779B2

Reaction notes

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