Methyl 4-chloroacetoacetate → HCID 178498740, compound

HRID 402649Notes

Reaction equation

HRID 402649 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[O:11][CH2:12][C:13](=[O:19])[C:14]=1[C:15]([O:17][CH3:18])=[O:16].ClCC(=O)CC(OC)=O.FC1C=C(F)C=CC=1N=C=O.[NH:40]1[C:48]2[C:43](=[CH:44][CH:45]=[CH:46][N:47]=2)[C:42]([CH:49]=O)=[CH:41]1.N1CCC[C@H]1C(O)=O>CC(O)C>[NH:40]1[C:48]2=[N:47][CH:46]=[CH:45][CH:44]=[C:43]2[C:42]([CH:49]=[C:12]2[O:11][C:10]([NH:9][C:3]3[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=3[F:1])=[C:14]([C:15]([O:17][CH3:18])=[O:16])[C:13]2=[O:19])=[CH:41]1

Participants

7

Reactant 5

HCID 36240Methyl 4-chloroacetoacetateHCID 145742L-ProlineHCID 5932582,4-Difluorophenyl isocyanateHCID 53728121H-Pyrrolo[2,3-b]pyridine-3-carbaldehydeHCID 86708340HCID 86708340, compound

Product 1

HCID 178498740HCID 178498740, compoundYield 75.5%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of methyl 2-[(2,4-difluorophenyl)amino]-4-oxo-4,5-dihydrofuran-3-carboxylate (0.27 g, 1.0 mmol) which similarly prepared according to the procedure described in the Example 2, First step using methyl 4-chloroacetoacetate and 2,4-difluorophenyl isocyanate, and 7-azaindole-3-carboxaldehyde (0.15 g, 1.0 mmol) in 2-propanol (5.0 mL), L-proline (0.023 g, 0.20 mmol) was added at ambient temperature. The mixture was refluxed for 12 h. Cooled to ambient temperature, the precipitate was collected by filtration, washed with ethanol and diisopropyl ether then dried to afford the titled compound as solid (0.30 g, y. 75%).

Workup

  1. additionwas added at ambient temperature
  2. temperatureThe mixture was refluxed for 12 h
  3. filtrationthe precipitate was collected by filtration
  4. washwashed with ethanol and diisopropyl ether
  5. customthen dried

Sources & evidence

ORD record
ord-4c23a98f7a514b1597e93d8e7901adbe
Source dataset
uspto-grants-2014_06
Patent number
US08742113B2

Reaction notes

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