1,2-Dichloroethane → HCID 53778668, compound

HRID 458873Notes

Reaction equation

HRID 458873 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]=[CH:8][C:9]([OH:11])=O)[CH:2]=1.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.Cl.[O:27]=[C:28]1[C:32]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[CH:31][C:30](=[O:39])[N:29]1[CH2:40][CH2:41][CH2:42][CH2:43][NH2:44]>ClCCl>[O:27]=[C:28]1[C:32]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[CH:31][C:30](=[O:39])[N:29]1[CH2:40][CH2:41][CH2:42][CH2:43][NH:44][C:9](=[O:11])[CH:8]=[CH:7][C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 1019843-(3-Pyridinyl)-2-propenoic acidHCID 17921877HCID 17921877, compound

Product 1

HCID 53778668HCID 53778668, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2.7 g (17.8 mmol) 3-(3-pyridyl)-acrylic acid and 1.8 g (17.8 mmol) TEA are suspended in 50 ml abs. dichloromethane and cooled to ca. 0° C. under moisture exclusion. 3.1 g (17.8 mmol) 88% HOBT and 3.4 g (17.8 mmol) EDC are added and the mixture is stirred for 30 min under ice cooling. 5.0 g (17.8 mmol) 4-(2,5-dioxo-3-phenyl-2,5-dihydropyrrol-1-yl)-butylamine hydrochloride are dissolved in 30 ml abs. dichloromethane and added dropwise under ice cooling. The mixture is stirred overnight at RT without further cooling. Subsequently, the batch is washed with 25 ml 1M NaOH and with 50 ml water. The organic phase is dried over sodium sulfate and the solvent is removed under vacuum. The resinous residue is chromatography pre-purified over silica gel with CHCl3/CH3OH (95/5) and further purified by flash chromatography with CHCl3/CH3OH (95/5). After withdraw of the solvent, this is crystallized from acetic acid ethyl ester: Colorless crystals with MP. 141–143° C.; Yield 0.6 g (9%).

Workup

  1. stirringThe mixture is stirred overnight at RT without further cooling
  2. washSubsequently, the batch is washed with 25 ml 1M NaOH and with 50 ml water
  3. dry with materialThe organic phase is dried over sodium sulfate
  4. customthe solvent is removed under vacuum
  5. custompre-purified over silica gel with CHCl3/CH3OH (95/5)
  6. customfurther purified by flash chromatography with CHCl3/CH3OH (95/5)
  7. customAfter withdraw of the solvent
  8. customthis is crystallized from acetic acid ethyl ester
  9. customwith MP. 141–143° C.

Sources & evidence

ORD record
ord-c4c814d56f924de4b4cf04eac1c480f4
Source dataset
uspto-grants-2007_03
Patent number
US07192967B1

Reaction notes

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