Ethyl Acetate → HCID 22632481, compound

HRID 2417533Notes

Reaction equation

HRID 2417533 reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][C:5]([C:6]([N:8]2[CH2:14][C:13]3[CH:15]=[CH:16][CH:17]=[CH:18][C:12]=3[NH:11][C:10](=[O:19])[CH2:9]2)=[O:7])=[CH:4][CH:3]=1.[H-].[Na+].CS(O[CH2:29][CH2:30][CH:31]1[CH2:36][CH2:35][N:34](C(OC(C)(C)C)=O)[CH2:33][CH2:32]1)(=O)=O.C(OCC)(=O)C>CN(C=O)C.Cl.O1CCOCC1>[Cl:1][C:2]1[CH:21]=[CH:20][C:5]([C:6]([N:8]2[CH2:14][C:13]3[CH:15]=[CH:16][CH:17]=[CH:18][C:12]=3[N:11]([CH2:29][CH2:30][CH:31]3[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]3)[C:10](=[O:19])[CH2:9]2)=[O:7])=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 8857Ethyl Acetate2×HCID 24758Sodium hydrideHCID 15229596tert-Butyl 4-(2-((methanesulfonyl)oxy)ethyl)piperidine-1-carboxylateHCID 226325544-(4-Chlorobenzoyl)-1,3,4,5-tetrahydrobenzo[e][1,4]diazepin-2-on

Product 1

HCID 22632481HCID 22632481, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 6228DimethylformamideSolventHCID 312751,4-DioxaneSolvent

Procedure

150 mg (0.50 mmol) of 4-(4-chlorobenzoyl)-1,3,4,5-tetrahydrobenzo[e][1,4]diazepin-2-on was dissolved in 10 ml of DMF. 24 mg (0.60 mmol) of sodium hydride was added to the obtained solution. After stirring at room temperature for 30 minutes, 184 g (0.60 mmol) of t-butyl 4-(2-((methylsulfonyl)oxy)ethyl)-1-piperidinecarboxylate was added to the obtained mixture, and they were stirred at 70° C. overnight. After the treatment with ethyl acetate as the extracting solvent by an ordinary method, the obtained crude product was dissolved in 10 ml of 4N solution of hydrogen chloride in dioxane, and the obtained solution was stirred overnight. After the treatment with ethyl acetate as the extracting solvent by an ordinary method, the title compound was obtained.

Workup

  1. stirringwere stirred at 70° C. overnight
  2. stirringthe obtained solution was stirred overnight

Sources & evidence

ORD record
ord-682d6a908bd64813a584317c28b15732
Source dataset
uspto-grants-2004_11
Patent number
US06825191B2

Reaction notes

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