Cyclopropylacetylene → HCID 86758856, compound

HRID 1060900Notes

Reaction equation

HRID 1060900 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]([NH:17][S:18]([CH2:20][CH:21]([CH2:23]C)[CH3:22])=[O:19])([C:11]2[N:12](C)[CH:13]=[N:14][CH:15]=2)C)=[CH:5][C:4]=1[F:25])#[N:2].[CH:26]1([C:29]#[C:30][Mg]Br)[CH2:28][CH2:27]1.C1(C#C)CC1.C([Mg]Br)C>C1COCC1.CCOCC>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:11]2[N:12]([C:30]#[C:29][CH:26]3[CH2:28][CH2:27]3)[CH:13]=[N:14][CH:15]=2)=[N:17][S:18]([CH2:20][CH:21]([CH3:23])[CH3:22])=[O:19])=[CH:5][C:4]=1[F:25])#[N:2]

Participants

7

Reactant 4

HCID 138823CyclopropylacetyleneHCID 18629437HCID 18629437, compoundHCID 178418443HCID 178418443, compoundHCID 178419643HCID 178419643, compound

Product 1

HCID 86758856HCID 86758856, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-[1-(4-cyano-3-fluoro-phenyl)-1-(3-methyl-3H-imidazol-4-yl)-ethyl]-2ethylpropanesulfinamide (Example 1, Step I) (0.50 g, 1.50 mmol) in THF (12 mL) at 0° C. in an ice-H2O bath was added cyclopropylethynyl magnesium bromide (3 mL of a 2M solution in Et2O prepared from cyclopropyl acetylene and ethyl magnesium bromide). Grignard reagent was added until the reaction mixture color remained dark brown/black. After 1 h the reaction mixture was quenched with H2O, diluted with CH2Cl2 and aqueous saturated NaHCO3 solution, layers separated, the aqueous layer washed with CH2Cl2 (2×), the organics combined, and dried (MgSO4). Filtration and concentration in vacuo gave the title compound as a 77/22 ratio of diastereomers.

Workup

  1. customAfter 1 h the reaction mixture was quenched with H2O
  2. additiondiluted with CH2Cl2 and aqueous saturated NaHCO3 solution, layers
  3. customseparated
  4. washthe aqueous layer washed with CH2Cl2 (2×)
  5. dry with materialdried (MgSO4)
  6. filtrationFiltration and concentration in vacuo

Sources & evidence

ORD record
ord-bd42b425e1614758a545810f8e981ef3
Source dataset
uspto-grants-2003_02
Patent number
US06525074B2

Reaction notes

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