Chloroacetyl chloride → HCID 178498727, compound

HRID 402653Notes

Reaction equation

HRID 402653 reaction equation
[CH:1]1([NH:4][C:5]2[O:6][CH2:7][C:8](=[O:14])[C:9]=2[C:10]([O:12][CH3:13])=[O:11])[CH2:3][CH2:2]1.C(OC)(=O)CC(OC)=O.ClCC(Cl)=O.C1(N)CC1.[NH:33]1[C:41]2[C:36](=[CH:37][CH:38]=[CH:39][N:40]=2)[C:35]([CH:42]=O)=[CH:34]1.N1CCC[C@H]1C(O)=O>C(O)C>[NH:33]1[C:41]2=[N:40][CH:39]=[CH:38][CH:37]=[C:36]2[C:35]([CH:42]=[C:7]2[O:6][C:5]([NH:4][CH:1]3[CH2:2][CH2:3]3)=[C:9]([C:10]([O:12][CH3:13])=[O:11])[C:8]2=[O:14])=[CH:34]1

Participants

8

Reactant 6

HCID 6577Chloroacetyl chlorideHCID 7943Dimethyl malonateHCID 69828CyclopropylamineHCID 145742L-ProlineHCID 53728121H-Pyrrolo[2,3-b]pyridine-3-carbaldehydeHCID 86708342HCID 86708342, compound

Product 1

HCID 178498727HCID 178498727, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of methyl 2-(cyclopropylamino)-4-oxo-4,5-dihydrofuran-3-carboxylate (0.50 g, 2.5 mmol) which similarly prepared according to the procedure described in the Example 4, First step using dimethyl malonate, chloroacetyl chloride and cyclopropylamine, and 7-azaindole-3-carboxaldehyde (0.37 g, 2.5 mmol) in ethanol (6.0 mL), L-proline (0.029 g, 0.25 mmol) was added at ambient temperature. The mixture was refluxed for 16 h. Cooled to ambient temperature, the precipitate was collected by filtration, washed with methanol then dried to afford the titled compound as solid (0.012 g, y. 30%).

Workup

  1. additionwas added at ambient temperature
  2. temperatureThe mixture was refluxed for 16 h
  3. filtrationthe precipitate was collected by filtration
  4. washwashed with methanol
  5. customthen dried

Sources & evidence

ORD record
ord-bacc73a858aa4a20aabadbc3f22e1ab2
Source dataset
uspto-grants-2014_06
Patent number
US08742113B2

Reaction notes

Loading…