Acetone → HCID 178490642, compound

HRID 538827Notes

Reaction equation

HRID 538827 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:24][CH3:25])=[C:6]([C:8](=[N:21][C:22]#[N:23])/[N:9]=[C:10]2\[S:11][CH:12]=[C:13]([CH3:20])[N:14]\2[CH2:15][CH:16]2[CH2:19][CH2:18][CH2:17]2)[CH:7]=1.C([N-]C(C)C)(C)C.[Li+].[CH3:34][C:35]([CH3:37])=[O:36].[Cl-].[NH4+]>O1CCCC1.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:24][CH3:25])=[C:6]([C:8](=[N:21][C:22]#[N:23])/[N:9]=[C:10]2\[S:11][C:12]([C:35]([OH:36])([CH3:37])[CH3:34])=[C:13]([CH3:20])[N:14]\2[CH2:15][CH:16]2[CH2:19][CH2:18][CH2:17]2)[CH:7]=1

Participants

7

Reactant 4

HCID 180AcetoneHCID 25517Ammonium ChlorideHCID 2724682Lithium diisopropylamideHCID 178490643HCID 178490643, compound

Product 1

HCID 178490642HCID 178490642, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Example 110D (101 mg, 0.269 mmol) in anhydrous tetrahydrofuran (4 mL) at −78° C. was added lithium diisopropylamide (2 M, 0.404 mL). After 5 min acetone (46.9 mg, 0.808 mmol) was added and the reaction was stirred for 0.5 hrs. Saturated ammonium chloride solution (2 mL) was added to quench the reaction at this temperature. The reaction mixture was diluted with water and extracted with ethyl acetate (3×10 mL). The organic layers were combined, washed with brine, dried with sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography using an Analogix® Intelliflash280™ (SiO2, 0-20% ethyl acetate in hexane) to afford the title compound (65 mg, 86%). 1H NMR (300 MHz, CHLOROFORM-D) δ ppm 1.67 (s, 6H) 1.81-1.94 (m, 4H) 2.00-2.08 (m, 2H) 2.50 (s, 3H) 2.68-2.81 (m, 1H) 3.91 (s, 3H) 4.30 (d, J=7.12 Hz, 2H) 6.91-6.96 (m, 1H) 7.33-7.38 (m, 2H); MS (DCI/NH3) m/z 433 (M+H)+. Anal. calcd C21H25ClN4O2S.0.6 EtOH: C, 57.95; H, 6.19; N, 12.24. Found: C, 57.86; H, 6.13; N, 11.85.

Workup

  1. customto quench
  2. customthe reaction at this temperature
  3. extractionextracted with ethyl acetate (3×10 mL)
  4. washwashed with brine
  5. dry with materialdried with sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-491155f54cf0498ca329648b6766b49e
Source dataset
uspto-grants-2014_10
Patent number
US08865753B2

Reaction notes

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