Sodium hydride → HCID 21993956, compound

HRID 1978495Notes

Reaction equation

HRID 1978495 reaction equation
COP([CH2:7][C:8](=[O:24])[CH2:9][CH2:10][CH:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]1)(OC)=O.[H-].[Na+].[N:27]1[CH:28]=[C:29]2[N:38]3[C:33](=[CH:34][CH:35]=[CH:36][C:37]=13)[S:32][C:31]([CH:39]=O)=[CH:30]2>C1(C)C=CC=CC=1.CN(C)C=O.O>[C:20]([O:19][C:17]([N:14]1[CH2:13][CH2:12][CH:11]([CH2:10][CH2:9][C:8](=[O:24])/[CH:7]=[CH:39]/[C:31]2[S:32][C:33]3[N:38]4[C:29](=[CH:28][N:27]=[C:37]4[CH:36]=[CH:35][CH:34]=3)[CH:30]=2)[CH2:16][CH2:15]1)=[O:18])([CH3:21])([CH3:22])[CH3:23]

Participants

7

Reactant 3

HCID 24758Sodium hydrideHCID 21993678HCID 21993678, compoundHCID 219941445-Thia-1,8b-diazaacenaphthylene-4-carbaldehyde

Product 1

HCID 21993956HCID 21993956, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolvent2×HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4.77 g (13.1 mM) of tert-butyl 4-[4-(dimethoxyphosphoryl)-3-oxobutyl]piperidine-1-carboxylate in 50 ml of toluene was added 0.48 g (12.0 mM) of a 60% suspension of sodium hydride in liquid paraffin at room temperature, and the mixture was stirred at the prevailing temperature for 2 hours. This reaction mixture was added to a solution of the above crude 5-thia-1,8b-diazaacenaphthylene-4-carbaldehyde in N,N-dimethylformamide (30 ml)-toluene (50 ml) with ice-cooling and the mixture was stirred at the prevailing temperature for 3 hours. This reaction mixture was poured in water and extracted with 3 portions of ethyl acetate. The organic layers were pooled and dried over MgSO4 and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate to ethyl acetate/methanol : 9/1) to provide crude (E)-5-[1-(tert-butoxycarbonyl)piperidin-4-yl]-1-(5-thia-1,8b-diazaacenaphthylen-4-yl)-1-penten-3-one. This crude product was not purified but used as it was in the next reaction.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at the prevailing temperature for 3 hours
  3. extractionextracted with 3 portions of ethyl acetate
  4. dry with materialdried over MgSO4
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate to ethyl acetate/methanol : 9/1)

Sources & evidence

ORD record
ord-ec0688b82ac64bbab5639e994ede7f05
Source dataset
uspto-grants-2001_05
Patent number
US06235731B1

Reaction notes

Loading…