Phenyl isocyanate → HCID 178498705, compound

HRID 402621Notes

Reaction equation

HRID 402621 reaction equation
[O:1]=[C:2]1[CH2:6][O:5][C:4]([NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10]C=2)=[C:3]1[C:14]([O:16][CH3:17])=[O:15].ClCC(=O)CC(OC)=O.C1(N=C=O)C=CC=CC=1.[NH:36]1[C:44]2[C:39](=[CH:40][CH:41]=[CH:42][N:43]=2)[C:38]([CH:45]=O)=[CH:37]1.N1CCCCC1>CO>[NH:36]1[C:44]2=[N:43][CH:42]=[CH:41][CH:40]=[C:39]2[C:38]([CH:45]=[C:6]2[O:5][C:4]([N:7]3[CH2:8][CH2:13][CH2:12][CH2:11][CH2:10]3)=[C:3]([C:14]([O:16][CH3:17])=[O:15])[C:2]2=[O:1])=[CH:37]1

Participants

7

Reactant 5

HCID 7672Phenyl isocyanateHCID 8082PiperidineHCID 36240Methyl 4-chloroacetoacetateHCID 53728121H-Pyrrolo[2,3-b]pyridine-3-carbaldehydeHCID 18801993HCID 18801993, compound

Product 1

HCID 178498705HCID 178498705, compoundYield 11%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 4-oxo-2-(phenylamino)-4,5-dihydrofuran-3-carboxylate (0.047 g, 0.20 mmol) which similarly prepared according to the procedure described in the Example 2, First step using methyl 4-chloroacetoacetate and phenyl isocyanate, and 7-azaindole-3-carboxaldehyde (0.029 g, 0.20 mmol) in methanol (1.0 mL), piperidine (0.022 mL, 0.22 mmol) was added at ambient temperature. The mixture was refluxed for 5 days. Cooled to ambient temperature, the precipitate was collected by filtration, then purified by preparative HPLC, collected former fraction to afford the titled compound as solid (0.0075 g, y. 11%).

Workup

  1. additionwas added at ambient temperature
  2. temperatureThe mixture was refluxed for 5 days
  3. filtrationthe precipitate was collected by filtration
  4. custompurified by preparative HPLC
  5. customcollected former fraction

Sources & evidence

ORD record
ord-23f2b69eedfb47a39ed73ad3c34f2599
Source dataset
uspto-grants-2014_06
Patent number
US08742113B2

Reaction notes

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