Chloroacetyl chloride → HCID 178459413, compound

HRID 402685Notes

Reaction equation

HRID 402685 reaction equation
[OH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9]2[O:10][CH2:11][C:12](=[O:20])[C:13]=2[C:14]([O:16][CH:17]([CH3:19])[CH3:18])=[O:15])[CH2:4][CH2:3]1.C(OC(C)C)(=O)CC(OC(C)C)=O.ClCC(Cl)=O.NC[C@H]1CC[C@H](O)CC1.[NH:48]1[C:56]2[C:51](=[CH:52][CH:53]=[CH:54][N:55]=2)[C:50]([CH:57]=O)=[CH:49]1.N1CCC[C@H]1C(O)=O>CC(O)C>[NH:48]1[C:56]2=[N:55][CH:54]=[CH:53][CH:52]=[C:51]2[C:50]([CH:57]=[C:11]2[O:10][C:9]([NH:8][C@H:5]3[CH2:6][CH2:7][C@H:2]([OH:1])[CH2:3][CH2:4]3)=[C:13]([C:14]([O:16][CH:17]([CH3:18])[CH3:19])=[O:15])[C:12]2=[O:20])=[CH:49]1

Participants

8

Reactant 6

HCID 6577Chloroacetyl chlorideHCID 83223Diisopropyl malonateHCID 145742L-ProlineHCID 53728121H-Pyrrolo[2,3-b]pyridine-3-carbaldehydeHCID 178459412HCID 178459412, compoundHCID 178511287HCID 178511287, compound

Product 1

HCID 178459413HCID 178459413, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of isopropyl 2-[(trans-4-hydroxycyclohexyl)amino]-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 trans-4-aminomethylcyclohexanol (0.056 mg, 0.49 mmol) in 2-propanol (1.0 mL) was stirred at ambient temperature for 20 h. To this reaction mixture, 7-azaindole-3-carboxaldehyde (0.065 g, 0.44 mmol) and L-proline (0.0050 g, 0.044 mmol) were added then the mixture was refluxed for further 1.5 days. The precipitate was collected by filtration, washed with hot ethanol. The solid was washed with hexane then dried to afford isopropyl 5-[(1H-pyrrolo[2,3-b]pyridin-3-yl)methylene]-2-[(trans-4-hydroxycyclohexyl)amino]-4-oxo-4,5-dihydrofuran-3-carboxylate as solid (0.0076 g, y. 4%).

Workup

  1. temperaturethe mixture was refluxed for further 1.5 days
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with hot ethanol
  4. washThe solid was washed with hexane
  5. customthen dried

Sources & evidence

ORD record
ord-f848dc277f4d4096b0c6d02fa4c01b3e
Source dataset
uspto-grants-2014_06
Patent number
US08742113B2

Reaction notes

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