Chloroacetyl chloride → HCID 178498766, compound

HRID 402660Notes

Reaction equation

HRID 402660 reaction equation
[CH:1]1([CH2:4][NH:5][C:6]2[O:7][CH2:8][C:9](=[O:15])[C:10]=2[C:11]([O:13][CH3:14])=[O:12])[CH2:3][CH2:2]1.C(OC)(=O)CC(OC)=O.ClCC(Cl)=O.C1(CN)CC1.[NH:35]1[C:43]2[C:38](=[CH:39][CH:40]=[CH:41][N:42]=2)[C:37]([CH:44]=O)=[CH:36]1.N1CCC[C@H]1C(O)=O>C(O)C>[NH:35]1[C:43]2=[N:42][CH:41]=[CH:40][CH:39]=[C:38]2[C:37]([CH:44]=[C:8]2[O:7][C:6]([NH:5][CH2:4][CH:1]3[CH2:3][CH2:2]3)=[C:10]([C:11]([O:13][CH3:14])=[O:12])[C:9]2=[O:15])=[CH:36]1

Participants

8

Reactant 6

HCID 6577Chloroacetyl chlorideHCID 7943Dimethyl malonateHCID 75646CyclopropanemethanamineHCID 145742L-ProlineHCID 53728121H-Pyrrolo[2,3-b]pyridine-3-carbaldehydeHCID 86708351HCID 86708351, compound

Product 1

HCID 178498766HCID 178498766, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of methyl 2-[(cyclopropylmethyl)amino]-4-oxo-4,5-dihydrofuran-3-carboxylate (0.30 g, 1.4 mmol) which similarly prepared according to the procedure described in the Example 4, First step using dimethyl malonate, chloroacetyl chloride and cyclopropylmethylamine, and 7-azaindole-3-carboxaldehyde (0.21 g, 1.4 mmol) in ethanol (10 mL), L-proline (0.016 g, 0.14 mmol) was added at ambient temperature. The mixture was refluxed for 3 days. Cooled to ambient temperature, the precipitate was collected by filtration, washed with methanol then dried to afford the titled compound as solid (0.065 g, y. 14%).

Workup

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

Sources & evidence

ORD record
ord-bdd8706af25a4daa866c821560d6bcbd
Source dataset
uspto-grants-2014_06
Patent number
US08742113B2

Reaction notes

Loading…