Chloroacetyl chloride → HCID 178459407, compound

HRID 402689Notes

Reaction equation

HRID 402689 reaction equation
C(O[C:5]1[O:6][CH2:7][C:8](=[O:16])[C:9]=1[C:10]([O:12][CH:13]([CH3:15])[CH3:14])=[O:11])(C)C.C(OC(C)C)(=O)CC(OC(C)C)=O.ClCC(Cl)=O.[CH:35]1([NH2:38])[CH2:37][CH2:36]1.[NH:39]1[C:47]2[C:42](=[CH:43][CH:44]=[CH:45][N:46]=2)[C:41]([CH:48]=O)=[CH:40]1.N1CCCCC1>CC(O)C>[NH:39]1[C:47]2=[N:46][CH:45]=[CH:44][CH:43]=[C:42]2[C:41]([CH:48]=[C:7]2[O:6][C:5]([NH:38][CH:35]3[CH2:37][CH2:36]3)=[C:9]([C:10]([O:12][CH:13]([CH3:14])[CH3:15])=[O:11])[C:8]2=[O:16])=[CH:40]1

Participants

8

Reactant 6

HCID 6577Chloroacetyl chlorideHCID 8082PiperidineHCID 69828CyclopropylamineHCID 83223Diisopropyl malonateHCID 53728121H-Pyrrolo[2,3-b]pyridine-3-carbaldehydeHCID 51050080Isopropyl 2-isopropoxy-4-oxo-4,5-dihydrofuran-3-carboxylate

Product 1

HCID 178459407HCID 178459407, compoundYield 1.3%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of isopropyl 2-isopropoxy-4-oxo-4,5-dihydrofuran-3-carboxylate (0.10 g, 0.44 mmol) which similarly prepared according to the procedure described in the Example 74, Third step using diisopropyl malonate and chloroacetyl chloride, and cyclopropylamine (0.034 mL, 0.48 mmol) in 2-propanol (2.0 mL) was stirred at ambient temperature for 14 h. To this reaction mixture, 7-azaindole-3-carboxaldehyde (0.065 g, 0.44 mmol) and piperidine (0.0044 mL, 0.044 mmol) were added then the mixture was refluxed for further 12 days. Cooled to ambient temperature, the reaction mixture was purified by preparative HPLC to afford the titled compound as solid (0.0020 g, y. 1%).

Workup

  1. temperaturethe mixture was refluxed for further 12 days
  2. temperatureCooled to ambient temperature
  3. customthe reaction mixture was purified by preparative HPLC

Sources & evidence

ORD record
ord-853605e8263a4041bda9d128e03a215d
Source dataset
uspto-grants-2014_06
Patent number
US08742113B2

Reaction notes

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