Ethanol → HCID 54239630, compound

HRID 2289518Notes

Reaction equation

HRID 2289518 reaction equation
[BH4-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[N:19][C:20]([N:28]2[CH2:33][CH2:32][C:31](=[O:34])[CH2:30][CH2:29]2)=[N:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[CH3:18])=[CH:6][CH:5]=1.[Cl-].[NH4+].[CH2:37](O)C>>[F:3][C:4]1[CH:5]=[CH:6][C:7]([NH:10][C:11](=[N:19][C:20]([N:28]2[CH2:33][CH2:32][CH:31]([OH:34])[CH2:30][CH2:29]2)=[N:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:12]2[C:17]([CH3:37])=[CH:16][CH:15]=[CH:14][C:13]=2[CH3:18])=[CH:8][CH:9]=1

Participants

5

Reactant 4

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 54201843HCID 54201843, compound

Product 1

HCID 54239630HCID 54239630, compoundYield 45%

Procedure

Sodium borohydride (0.006 g, 0.152 mmol) was added to a solution of the product from Example 8, free base, (0.067 g, 0.152 mmol) in ethanol (6 mL) and the mixture was stirred at room temperature for 2 hours. Saturated ammonium chloride was added and the mixture was extracted with methylene chloride (twice). The organic layer was dried (potassium carbonate), filtered, and concentrated. The residue was dissolved in dioxane and hydrogen chloride (g) was bubbled through. After removal of volatiles, the salt obtained was purified by silica gel flash chromatography to give the title compound (0.033 g, 45%), hydrochloride salt, as an off-white solid.

Workup

  1. extractionthe mixture was extracted with methylene chloride (twice)
  2. dry with materialThe organic layer was dried (potassium carbonate)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in dioxane
  6. customhydrogen chloride (g) was bubbled through
  7. customAfter removal of volatiles
  8. customthe salt obtained
  9. customwas purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-48200b41c98a4997809dbb042ef6e9cb
Source dataset
uspto-grants-2000_07
Patent number
US06093733

Reaction notes

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