Tetrahydrofuran → HCID 70247983, compound

HRID 1978506Notes

Reaction equation

HRID 1978506 reaction equation
O(P([CH2:17][S:18]([NH:21][CH2:22][CH:23]1[CH2:28][CH2:27][N:26]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:25][CH2:24]1)(=[O:20])=[O:19])(OC1C=CC=CC=1)=O)C1C=CC=CC=1.O1CCCC1.[H-].[Na+].[N:43]1[CH:44]=[C:45]2[N:54]3[C:49](=[CH:50][CH:51]=[CH:52][C:53]=13)[S:48][C:47]([CH:55]=O)=[CH:46]2>C1(C)C=CC=CC=1.CN(C)C=O.O>[C:32]([O:31][C:29]([N:26]1[CH2:25][CH2:24][CH:23]([CH2:22][NH:21][S:18](/[CH:17]=[CH:55]/[C:47]2[S:48][C:49]3[N:54]4[C:45](=[CH:44][N:43]=[C:53]4[CH:52]=[CH:51][CH:50]=3)[CH:46]=2)(=[O:19])=[O:20])[CH2:28][CH2:27]1)=[O:30])([CH3:33])([CH3:34])[CH3:35]

Participants

8

Reactant 4

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 21993912HCID 21993912, compoundHCID 219941445-Thia-1,8b-diazaacenaphthylene-4-carbaldehyde

Product 1

HCID 70247983HCID 70247983, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolvent2×HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2.16 g (4.11 mM) of tert-butyl 4-(diphenoxyphosphorylmethanesulfonylaminomethyl)-piperidine-1-carboxylate in toluene (20 ml)-tetrahydro-furan (20 ml) was added 0.33 g (8.23 mM) of a 60% suspension of sodium hydride in liquid paraffin at room temperature and the mixture was stirred at the prevailing temperature for 1 hour. This reaction mixture was added to a solution of the above crude 5-thia-1,8b-diazaacenaphthylene-4-carbaldehyde in N,N-dimethylformamide (10 ml)-toluene (50 ml) at room temperature and the mixture was stirred at the prevailing temperature for 0.5 hour. 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 subjected to silica gel column chromatography (ethyl acetate to ethyl acetate/methanol : 9/1) to provide crude (E)-N-[1-(tert-butoxycarbonyl)piperidin-4-ylmethyl]-2-(5-thia-1,8b-diazaacenaphthylen-4-yl)vinylsulfonamide. To this crude product was added 1 ml of concentrated hydrochloric acid, and the mixture was stirred at room temperature for 30 minutes. To this reaction mixture was added ethanol, followed by stirring, and the resulting precipitate was recovered and washed serially with ethanol and diethyl ether to provide the title compound.

Workup

  1. stirringthe mixture was stirred at the prevailing temperature for 0.5 hour
  2. extractionextracted with 3 portions of ethyl acetate
  3. dry with materialdried over MgSO4
  4. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-b934f0b1d06b4795ad5edaf1a9248fcb
Source dataset
uspto-grants-2001_05
Patent number
US06235731B1

Reaction notes

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