Diisopropylamine → HCID 178506292, compound

HRID 921517Notes

Reaction equation

HRID 921517 reaction equation
C([Li])CCC.C(NC(C)C)(C)C.F[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1.[F:20][C:21]([F:28])([F:27])[C:22](OCC)=O.O.[NH2:30][NH2:31]>CCCCCC.O1CCCC1.O>[F:20][C:21]([F:28])([F:27])[C:22]1[C:19]2[C:14](=[N:15][CH:16]=[CH:17][CH:18]=2)[NH:31][N:30]=1

Participants

9

Reactant 5

HCID 7912DiisopropylamineHCID 97462-FluoropyridineHCID 9794Ethyl trifluoroacetateHCID 24654Hydrazine hydrate (1:1)HCID 178418339Butyllithium

Product 1

HCID 178506292HCID 178506292, compoundYield 85%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent4×HCID 8058HexaneSolvent

Procedure

Normal-butyllithium (a 2.6 M solution in hexane, 87.2 mL) was dropwise added to a solution of N,N-diisopropylamine (25.0 g) in tetrahydrofuran (hereinafter referred to as THF, 300 mL) under a nitrogen atmosphere at −5 to 0° C., and a solution of 2-fluoropyridine (25 g) in THF (50 mL) was dropwise added thereto at −78° C., followed by stirring for 1 hr. Subsequently, a solution of ethyl trifluoroacetate (47.6 g) in THF (50 mL) was dropwise added to the reaction solution at −78° C., followed by stirring at the same temperature for 1 hr. Hydrazine monohydrate (41.3 g) was added thereto, followed by stirring at 60° C. for 6 hr. Water (500 mL) was added to the reaction solution, followed by stirring at 100° C. for 30 min. The precipitate was collected by filtration and dried under reduced pressure to obtain a compound (1a) (32.8 g, 85%) as a white solid.

Workup

  1. customat −5 to 0° C.
  2. customat −78° C.
  3. stirringby stirring at the same temperature for 1 hr
  4. stirringby stirring at 60° C. for 6 hr
  5. stirringby stirring at 100° C. for 30 min
  6. filtrationThe precipitate was collected by filtration
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-87452b9337374821bb98996f6d9dbc13
Source dataset
uspto-grants-2016_03
Patent number
US09273045B2

Reaction notes

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