Dimethyl Sulfoxide → HCID 67280305, compound

HRID 1693290Notes

Reaction equation

HRID 1693290 reaction equation
[OH:1][CH:2]1[C:11]2[CH2:10][S:9][N:8]=[C:7]([N:12]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C:6]3=[N:27][N:28]([CH2:30][C:31]4[C:36]([CH3:37])=[C:35]([O:38][CH3:39])[C:34]([CH3:40])=[CH:33][N:32]=4)[N:29]=[C:4]([C:5]=23)[CH2:3]1.CS(C)=O.[C:45](OC(=O)C)(=[O:47])[CH3:46]>C(OCC)(=O)C>[C:45]([O:1][C:2]1[C:11]2[CH2:10][S:9][N:8]=[C:7]([N:12]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C:6]3=[N:27][N:28]([CH2:30][C:31]4[C:36]([CH3:37])=[C:35]([O:38][CH3:39])[C:34]([CH3:40])=[CH:33][N:32]=4)[N:29]=[C:4]([C:5]=23)[CH:3]=1)(=[O:47])[CH3:46]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 7918Acetic AnhydrideHCID 86641323HCID 86641323, compound

Product 1

HCID 67280305HCID 67280305, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture composed of di-tert-butyl {8-hydroxy-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]-2,7,8,9-tetrahydro-6-thia-1,2,3,5-tetraazabenzo[cd]azulen-4-yl}imidodicarbonate of Example 32 (778 mg), dimethyl sulfoxide (10 mL) and acetic anhydride (1 mL) was stirred in a nitrogen atmosphere at room temperature for 12 hours. After confirming that the raw material disappeared, the reaction mixture was diluted with ethyl acetate and sequentially washed with water and brine. The organic layer was dried over anhydrous sodium sulfate and filtered. Then, the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate-hexane) to obtain the title compound (507 mg, 61%) as an oil.

Workup

  1. washsequentially washed with water and brine
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationThen, the filtrate was concentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate-hexane)

Sources & evidence

ORD record
ord-1b6d335d2fc7443f831e866f8beb19f9
Source dataset
uspto-grants-2012_04
Patent number
US08158638B2

Reaction notes

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