Methanol → HCID 67280016, compound

HRID 1693318Notes

Reaction equation

HRID 1693318 reaction equation
[BH4-].[Na+].[F:3][C:4]1([F:44])[C:13]2=[N:14][N:15]([CH2:17][C:18]3[C:23]([CH3:24])=[C:22]([O:25][CH3:26])[C:21]([CH3:27])=[CH:20][N:19]=3)[N:16]=[C:11]3[C:12]2=[C:6]([CH2:7][S:8][N:9]=[C:10]3[N:28](C(OC(C)(C)C)=O)C(OC(C)(C)C)=O)[C:5]1=[O:43].CO>O>[NH2:28][C:10]1[C:11]2[C:12]3[C:13](=[N:14][N:15]([CH2:17][C:18]4[C:23]([CH3:24])=[C:22]([O:25][CH3:26])[C:21]([CH3:27])=[CH:20][N:19]=4)[N:16]=2)[C:4]([F:44])([F:3])[CH:5]([OH:43])[C:6]=3[CH2:7][S:8][N:9]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 86641351HCID 86641351, compound

Product 1

HCID 67280016HCID 67280016, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

Sodium borohydride (6 mg) was added to a mixture composed of the above di-tert-butyl {9,9-difluoro-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]-8-oxo-2,7,8,9-tetrahydro-6-thia-1,2,3,5-tetraazabenzo[cd]azulen-4-yl}imidodicarbonate (41 mg) and methanol (2 ml) under ice-cooling, and the mixture was stirred at 0° C. for 30 minutes. Water was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with water. The organic layer was dried over sodium sulfate and filtered. Then, the filtrate was concentrated under reduced pressure. Dichloromethane (2 ml) and trifluoroacetic acid (0.5 ml) were added to the resulting residue, and the mixture was stirred at room temperature for four hours. The reaction mixture was concentrated under reduced pressure, and the resulting residue was purified by reversed phase liquid chromatography to obtain the title compound (8.7 mg, 42% in total from Example 110) as a solid.

Workup

  1. temperaturecooling
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationThen, the filtrate was concentrated under reduced pressure
  7. additionDichloromethane (2 ml) and trifluoroacetic acid (0.5 ml) were added to the resulting residue
  8. stirringthe mixture was stirred at room temperature for four hours
  9. concentrationThe reaction mixture was concentrated under reduced pressure
  10. customthe resulting residue was purified by reversed phase liquid chromatography

Sources & evidence

ORD record
ord-3aa847c491914444b4260611c176e1c5
Source dataset
uspto-grants-2012_04
Patent number
US08158638B2

Reaction notes

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