Hydrochloric Acid → HCID 89525987, compound

HRID 1621018Notes

Reaction equation

HRID 1621018 reaction equation
Cl[C:2]1[N:6]([CH3:7])[C:5]2[CH:8]=[CH:9][CH:10]=[CH:11][C:4]=2[N:3]=1.[CH:12]1([C:16]#[N:17])[CH2:15][CH2:14][CH2:13]1.C[Si](C)(C)[N-][Si](C)(C)C.[K+].Cl>C1(C)C=CC=CC=1>[CH3:7][N:6]1[C:5]2[CH:8]=[CH:9][CH:10]=[CH:11][C:4]=2[N:3]=[C:2]1[C:12]1([C:16]#[N:17])[CH2:15][CH2:14][CH2:13]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 78148CyanocyclobutaneHCID 6630802-chloro-1-methyl-1H-1,3-benzodiazoleHCID 3251421Potassium bis(trimethylsilyl)amide

Product 1

HCID 89525987HCID 89525987, compoundYield 41.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of Example 275A (1.90 g, 11.4 mmol) in toluene (30 mL) was added cyclobutanecarbonitrile (1.01 g, 12.5 mmol) and potassium hexamethyldisilazide (34.2 mL, 17.1 mmol). The reaction mixture was stirred at room temperature overnight. The mixture was poured into 1N HCl solution (50 mL) and the aqueous layer was extracted with EtOAc (3×20 mL). The combined layers were washed with brine (100 mL), dried over MgSO4, filtered, and concentrated. The residue was purified by prep. TLC on silicagel (eluted with EtOAc:petroleum ether=1:10) to give the title compound (1.0 g, 4.69 mmol, 41.1% yield) as a white solid. MS: MS (M+H)+; 1H NMR (400 MHz, CDCl3): δ 7.80-7.78 (m, 1H), 7.36-7.30 (m, 3H), 3.83 (s, 3H), 3.13-3.05 (m, 2H), 2.99-2.92 (m, 2H), 2.48-2.41 (m, 1H), 2.24-2.18 (m, 1H).

Workup

  1. extractionthe aqueous layer was extracted with EtOAc (3×20 mL)
  2. washThe combined layers were washed with brine (100 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by prep
  7. washTLC on silicagel (eluted with EtOAc:petroleum ether=1:10)

Sources & evidence

ORD record
ord-aa307c2286b841ab9a95cce85969878e
Source dataset
uspto-grants-2014_07
Patent number
US08772500B2

Reaction notes

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