Acetone → HCID 68292684, compound

HRID 1504949Notes

Reaction equation

HRID 1504949 reaction equation
[Si]([C:5]#[N:6])(C)(C)C.[NH2:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH2:16][C:17]([NH:19][CH3:20])=[O:18])=[CH:10][CH:9]=1.[CH3:21][C:22]([CH3:24])=O>>[C:5]([C:22]([NH:7][C:8]1[CH:9]=[CH:10][C:11]([CH2:14][CH2:15][CH2:16][C:17]([NH:19][CH3:20])=[O:18])=[CH:12][CH:13]=1)([CH3:24])[CH3:21])#[N:6]

Participants

4

Reactant 3

HCID 180AcetoneHCID 82115Trimethylsilyl cyanideHCID 68292716HCID 68292716, compound

Product 1

HCID 68292684HCID 68292684, compound

Procedure

TMSCN (0.1 mL, 0.78 mmol) was added to a mixture of the compound 30 (50 mg, 0.26 mmol), acetone (0.12 mL, 1.56 mmol) and 12 (4 mg, 0.03 mmol) with stirring. The reaction mixture was stirred at 40° C. for 1 h, and concentrated in vacuo. The residue was diluted with aqNa2SO3, and extracted with ethyl acetate. The combined organic layers were washed with aqNa2SO3 and brine, dried over Na2SO4 and concentrated to dryness to give compound 31 as light yellow oil. The crude product was used directly for the next step without purification. 1H NMR (400 MHz, CDCl3) δ7.07 (d, 2H, J=8.4 Hz), 6.88 (d, 2H, J=8.4 Hz), 5.33 (br s, 1H), 2.79 (d, 3H, J=4.8 Hz), 2.59 (t, 2H, J=7.4 Hz), 2.16 (t, 2H, J=7.4 Hz), 1.85-1.95 (m, 2H), 1.68 (s, 6H).

Workup

  1. stirringThe reaction mixture was stirred at 40° C. for 1 h
  2. concentrationconcentrated in vacuo
  3. additionThe residue was diluted with aqNa2SO3
  4. extractionextracted with ethyl acetate
  5. washThe combined organic layers were washed with aqNa2SO3 and brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-3deadaddb6f74224b6cfa0efc838c424
Source dataset
uspto-grants-2015_12
Patent number
US09216957B2

Reaction notes

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