Trifluoroacetic acid → 2-[(4-Methoxy-3,5-dimethylpyridin-2-yl)methyl]-7,8-dihydro-2H-6-thia-1,2,3,5-tetraazaacenaphthylen-4-amine

HRID 1693267

Reaction equation

HRID 1693267 reaction equation
FC(F)(F)C(O)=O.[CH3:8][O:9][C:10]1[C:15]([CH3:16])=[CH:14][N:13]=[C:12]([CH2:17][N:18]2[C:28]3[C:29]4[C:20]([CH2:21][CH2:22][S:23][C:24]=4[N:25]=[C:26]([N:30](C(OC(C)(C)C)=O)C(OC(C)(C)C)=O)[N:27]=3)=[N:19]2)[C:11]=1[CH3:45].NC1N=C(Cl)C(C(O)CC=C)=C(Cl)N=1>ClCCl>[CH3:8][O:9][C:10]1[C:15]([CH3:16])=[CH:14][N:13]=[C:12]([CH2:17][N:18]2[C:28]3[C:29]4[C:20]([CH2:21][CH2:22][S:23][C:24]=4[N:25]=[C:26]([NH2:30])[N:27]=3)=[N:19]2)[C:11]=1[CH3:45]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 44476494Di-tert-butyl {2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]-7,8-dihydro-2H-6-thia-1,2,3,5-tetraazaacenaphthylen-4-yl}imidodicarbonateHCID 582011891-(2-Amino-4,6-dichloropyrimidin-5-yl)-3-buten-1-ol

Product 1

HCID 248112842-[(4-Methoxy-3,5-dimethylpyridin-2-yl)methyl]-7,8-dihydro-2H-6-thia-1,2,3,5-tetraazaacenaphthylen-4-amineYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (0.5 mL) was added to a mixture composed of di-tert-butyl {2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]-7,8-dihydro-2H-6-thia-1,2,3,5-tetraazaacenaphthylen-4-yl}imidodicarbonate of Step 10) of Example 1 (59 mg) and dichloromethane (2 mL) under cooling in an ice bath. Then, the ice bath was removed and the mixture was stirred for two hours. The reaction solution was concentrated under reduced pressure. Then, the resulting residue was dissolved in ethyl acetate and sequentially washed with a saturated sodium bicarbonate solution and brine. The organic layer was dried over anhydrous magnesium sulfate and filtered. Then, the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate-methanol) to obtain the title compound (26 mg, 85%) as a solid.

Workup

  1. temperatureunder cooling in an ice bath
  2. customThen, the ice bath was removed
  3. concentrationThe reaction solution was concentrated under reduced pressure
  4. dissolutionThen, the resulting residue was dissolved in ethyl acetate
  5. washsequentially washed with a saturated sodium bicarbonate solution and brine
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationThen, the filtrate was concentrated under reduced pressure
  9. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate-methanol)

Sources & evidence

ORD record
ord-7ef8da848ce94f32ba04049183ea6ea8
Source dataset
uspto-grants-2012_04
Patent number
US08158638B2

Linked notes

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