Chloroacetyl chloride → HCID 178498778, compound

HRID 402658Notes

Reaction equation

HRID 402658 reaction equation
[F:1][C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[CH2:4][NH:5][C:6]1[O:7][CH2:8][C:9](=[O:15])[C:10]=1[C:11]([O:13][CH3:14])=[O:12].C(OC)(=O)CC(OC)=O.ClCC(Cl)=O.FC1C=CC=CC=1CN.[NH:43]1[C:51]2[C:46](=[CH:47][CH:48]=[CH:49][N:50]=2)[C:45]([CH:52]=O)=[CH:44]1.N1CCC[C@H]1C(O)=O>C(O)C>[NH:43]1[C:51]2=[N:50][CH:49]=[CH:48][CH:47]=[C:46]2[C:45]([CH:52]=[C:8]2[O:7][C:6]([NH:5][CH2:4][C:3]3[CH:16]=[CH:17][CH:18]=[CH:19][C:2]=3[F:1])=[C:10]([C:11]([O:13][CH3:14])=[O:12])[C:9]2=[O:15])=[CH:44]1

Participants

8

Reactant 6

HCID 6577Chloroacetyl chlorideHCID 7943Dimethyl malonateHCID 666492-FluorobenzylamineHCID 145742L-ProlineHCID 53728121H-Pyrrolo[2,3-b]pyridine-3-carbaldehydeHCID 86708348HCID 86708348, compound

Product 1

HCID 178498778HCID 178498778, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of methyl 2-[(2-fluorobenzyl)amino]-4-oxo-4,5-dihydrofuran-3-carboxylate (0.35 g, 1.5 mmol) which similarly prepared according to the procedure described in the Example 4, First step using dimethyl malonate, chloroacetyl chloride and 2-fluorobenzylamine, and 7-azaindole-3-carboxaldehyde (0.22 g, 1.5 mmol) in ethanol (10 mL), L-proline (0.018 g, 0.15 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 (0.13 g, y. 24%).

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-46aee1c0d1d74cd1b92ba9d281cc7900
Source dataset
uspto-grants-2014_06
Patent number
US08742113B2

Reaction notes

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