Chloroacetyl chloride → propan-2-yl 2-(cyclohexylmethylamino)-4-oxo-5-(1H-pyrrolo[2,3-b]pyridin-3-ylmethylidene)furan-3-carboxylate

HRID 402684

Reaction equation

HRID 402684 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.[NH2:35][CH2:36][CH:37]1[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]1.[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.N1CCCCC1>CC(O)C>[NH:43]1[C:51]2=[N:50][CH:49]=[CH:48][CH:47]=[C:46]2[C:45]([CH:52]=[C:7]2[O:6][C:5]([NH:35][CH2:36][CH:37]3[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]3)=[C:9]([C:10]([O:12][CH:13]([CH3:14])[CH3:15])=[O:11])[C:8]2=[O:16])=[CH:44]1

Participants

8

Reactant 6

HCID 6577Chloroacetyl chlorideHCID 8082PiperidineHCID 76688CyclohexanemethylamineHCID 83223Diisopropyl malonateHCID 53728121H-Pyrrolo[2,3-b]pyridine-3-carbaldehydeHCID 51050080Isopropyl 2-isopropoxy-4-oxo-4,5-dihydrofuran-3-carboxylate

Product 1

HCID 178459409propan-2-yl 2-(cyclohexylmethylamino)-4-oxo-5-(1H-pyrrolo[2,3-b]pyridin-3-ylmethylidene)furan-3-carboxylateYield 20%

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 aminomethylcyclohexane (0.063 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 8 days. Cooled to ambient temperature, the reaction mixture was purified by preparative HPLC to afford the titled compound as solid (0.036 g, y. 19%).

Workup

  1. temperaturethe mixture was refluxed for further 8 days
  2. temperatureCooled to ambient temperature
  3. customthe reaction mixture was purified by preparative HPLC

Sources & evidence

ORD record
ord-20dde74e66a94bd095fda331e0a36e7d
Source dataset
uspto-grants-2014_06
Patent number
US08742113B2

Linked notes

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