Ammonium Chloride → HCID 59389304, compound

HRID 2357956Notes

Reaction equation

HRID 2357956 reaction equation
[CH2:1]([Mg]Br)[CH3:2].[CH3:5][O:6][C:7]1[N:12]2[N:13]=[C:14]([C:16]([F:22])([F:21])[C:17]([F:20])([F:19])[F:18])[CH:15]=[C:11]2[C:10]([CH:23]=[O:24])=[CH:9][CH:8]=1.[Cl-].[NH4+]>O1CCCC1>[OH:24][CH:23]([C:10]1[C:11]2[N:12]([N:13]=[C:14]([C:16]([F:22])([F:21])[C:17]([F:18])([F:19])[F:20])[CH:15]=2)[C:7]([O:6][CH3:5])=[CH:8][CH:9]=1)[CH2:1][CH3:2]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 59389347HCID 59389347, compoundHCID 178418443HCID 178418443, compound

Product 1

HCID 59389304HCID 59389304, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In an argon atmosphere, ethyl magnesium bromide (5.44 mL, 0.91 mol/L tetrahydrofuran solution) was added to a solution of the compound of Example 354 (1.24 g) in tetrahydrofuran (30 mL) at −78° C. The mixture was allowed to gradually warm to room temperature and was stirred at room temperature for 1 hour. Subsequently, a saturated aqueous ammonium chloride solution was added and the mixture was extracted with ethyl acetate (100 mL). The extract was washed sequentially with water and saturated brine and dried over anhydrous sodium sulfate. The extract was then concentrated and purified by amino-silica gel column chromatography (ethyl acetate) to afford the title compound as a pale yellow oil (1.41 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate (100 mL)
  2. washThe extract was washed sequentially with water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationThe extract was then concentrated
  5. custompurified by amino-silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-f695f50e49174ff3a01aeb09974ce61f
Source dataset
uspto-grants-2010_07
Patent number
US07763617B2

Reaction notes

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