Diisopropylamine → HCID 66618850, compound

HRID 406315Notes

Reaction equation

HRID 406315 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]([C:9](=[O:11])[CH3:10])[CH:6]=[CH:5][C:4]=1[N:12]1[CH:16]=[C:15]([CH3:17])[N:14]=[CH:13]1.C(NC(C)C)(C)C.[Li].C([Li])CCC.C(NC(C)C)(C)C.[Cl:38][CH2:39][CH2:40][CH2:41][CH:42]([C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][C:47]=1[C:52]([F:55])([F:54])[F:53])[C:43](Cl)=[O:44]>O1CCCC1>[Cl:38][CH2:39][CH2:40][CH2:41][CH:42]([C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][C:47]=1[C:52]([F:53])([F:54])[F:55])[C:43](=[O:44])[CH2:10][C:9]([C:7]1[CH:6]=[CH:5][C:4]([N:12]2[CH:16]=[C:15]([CH3:17])[N:14]=[CH:13]2)=[C:3]([O:2][CH3:1])[N:8]=1)=[O:11]

Participants

7

Reactant 5

HCID 7912DiisopropylamineHCID 45051747Lithium diisopropylamineHCID 58351063HCID 58351063, compoundHCID 66618770HCID 66618770, compoundHCID 178418339Butyllithium

Product 1

HCID 66618850HCID 66618850, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1-[6-methoxy-5-(4-methylimidazol-1-yl)pyridin-2-yl]ethanone obtained in Preparation Example 1-8 (412 mg) in tetrahydrofuran (10 ml) was added at −30° C. to a lithium diisopropylamine solution prepared from n-butyllithium (1.4 mL) and diisopropylamine (528 μL) in tetrahydrofuran (30 mL). After stirring at the same temperature for 30 minutes, 5-chloro-2-(2-trifluoromethylphenyl)valeric acid chloride (532 mg) was added and the mixture was stirred for 1.5 hours. After further stirring at room temperature for 30 minutes, the reaction was terminated with water, followed by dilution with ethyl acetate. The organic layer was washed with brine and dried over magnesium sulfate. The oil after concentration under reduced pressure was purified by silica gel chromatography (mobile phase:ethyl acetate/heptane=0 to 100%) to obtain the title compound (90 mg).

Workup

  1. stirringthe mixture was stirred for 1.5 hours
  2. stirringAfter further stirring at room temperature for 30 minutes
  3. customthe reaction was terminated with water
  4. washThe organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationThe oil after concentration under reduced pressure
  7. customwas purified by silica gel chromatography (mobile phase:ethyl acetate/heptane=0 to 100%)

Sources & evidence

ORD record
ord-01b16a04ece04c56acc44af3b2316b63
Source dataset
uspto-grants-2014_06
Patent number
US08754100B2

Reaction notes

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