Sodium methanethiolate → HCID 68865250, compound

HRID 494146Notes

Reaction equation

HRID 494146 reaction equation
[CH2:1]([O:8][C:9]1[C:17]2[C:16](=[O:18])[N:15]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)[N:14]=[C:13](Br)[C:12]=2[N:11]2[CH2:28][CH2:29][N:30]([CH3:33])[C:31](=[O:32])[C:10]=12)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:34][S-:35].[Na+]>CN(C=O)C>[CH2:1]([O:8][C:9]1[C:17]2[C:16](=[O:18])[N:15]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)[N:14]=[C:13]([S:35][CH3:34])[C:12]=2[N:11]2[CH2:28][CH2:29][N:30]([CH3:33])[C:31](=[O:32])[C:10]=12)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 4378561Sodium methanethiolateHCID 68866000HCID 68866000, compound

Product 1

HCID 68865250HCID 68865250, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 10-(benzyloxy)-4-bromo-2-(4-fluorobenzyl)-8-methyl-7,8-dihydropyrazino[1′,2′:1,5]pyrrolo[2,3-d]pyridazine-1,9(2H,6H)-dione (133 mg, 0.26 mmol) and sodium thiomethoxide (73 mg, 1.04 mmol) in anhydrous DMF (2.6 mL) was stirred at room temperature for 2 hours. The product mixture was concentrated under vacuum and the residue partitioned between chloroform and dilute hydrochloric acid. The organic phase was washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under vacuum. The residue was subjected to column chromatography on silica gel eluting with ethyl acetate. Collection and concentration of appropriate fractions afforded the title compound.

Workup

  1. concentrationThe product mixture was concentrated under vacuum
  2. customthe residue partitioned between chloroform and dilute hydrochloric acid
  3. washThe organic phase was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customCollection and concentration of appropriate fractions

Sources & evidence

ORD record
ord-02b183d85bf848508f89293690720096
Source dataset
uspto-grants-2009_05
Patent number
US07538112B2

Reaction notes

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