Thionyl Chloride → HCID 22479241, compound

HRID 1392176Notes

Reaction equation

HRID 1392176 reaction equation
O[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:34]=[CH:33][C:12]([CH2:13][C:14]23[C:22](=[O:23])[N:21]([C:24]4[CH:29]=[C:28]([Cl:30])[CH:27]=[C:26]([Cl:31])[CH:25]=4)[C:20](=[O:32])[N:19]2[CH2:18][CH2:17][CH2:16][CH2:15]3)=[CH:11][CH:10]=1.S(Cl)([Cl:37])=O>C(Cl)Cl>[Cl:37][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:34]=[CH:33][C:12]([CH2:13][C:14]23[C:22](=[O:23])[N:21]([C:24]4[CH:25]=[C:26]([Cl:31])[CH:27]=[C:28]([Cl:30])[CH:29]=4)[C:20](=[O:32])[N:19]2[CH2:18][CH2:17][CH2:16][CH2:15]3)=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 22479121HCID 22479121, compound

Product 1

HCID 22479241HCID 22479241, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-[4-[2-(hydroxymethyl)phenyl]benzyl]-8-(3,5-dichlorophenyl)-1,8-diazabicyclo[4.3.0]nonane-7,9-dione (0.318 g) in CH2Cl2 (5 mL) was added thionyl chloride (0.2 mL) and the mixture was stirred for 1 hour at room temperature. The mixture was concentrated and the residue was redissolved in CH2Cl2 (5 mL) and evaporated again. The residue was dried under vacuum to give 6-[4-[2-(chloromethyl)phenyl]benzyl]-8-(3,5-dichlorophenyl)-1,8-diazabicyclo[4.3.0]nonane-7,9-dione. (2) NaH (60% in oil, 0.090 mg) was added to a solution of N,N-dimethylethanolamine (0.58 mg) in DMF (5 mL) and the mixture was stirred for 30 minutes. To the reaction mixture was added a solution of the compound obtained above in DMF (2 mL) and the mixture was stirred overnight at room temperature. The mixture was cooled in ice-water and quenched with EtOAc/water. The organic layer was separated and washed with water and brine. It was dried, filtered, stripped and the residue was purified by chromatography (silica gel: CHCl3/MeOH: 50/1 to 30/1) to yield 84 mg of the titled compound. It was dissolved in MeOH and treated with 1N HCl/Et2O (2 mL). The mixture was evaporated and dried under vacuum to yield 88 mg of the hydrochloride of the titled compound. MS (m/z) 566 (MH+).

Workup

  1. concentrationThe mixture was concentrated
  2. dissolutionthe residue was redissolved in CH2Cl2 (5 mL)
  3. customevaporated again
  4. customThe residue was dried under vacuum

Sources & evidence

ORD record
ord-56e5e0195d8647daa1d6bcfda6287b90
Source dataset
uspto-grants-2008_03
Patent number
US07342012B2

Reaction notes

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