Water → HCID 178448639, compound

HRID 1931125Notes

Reaction equation

HRID 1931125 reaction equation
[CH2:1]([N:5]1[N:6]([CH3:28])[C:7]([C:24]([CH3:27])([CH3:26])[CH3:25])=[CH:8]/[C:9]/1=[N:10]\[C:11](=[O:23])[C:12]1[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[CH:14][C:13]=1F)[CH2:2][CH2:3][CH3:4].[SH:29][CH2:30][CH:31]([OH:33])[CH3:32].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[CH2:1]([N:5]1[N:6]([CH3:28])[C:7]([C:24]([CH3:26])([CH3:27])[CH3:25])=[CH:8]/[C:9]/1=[N:10]\[C:11](=[O:23])[C:12]1[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[CH:14][C:13]=1[S:29][CH2:30][CH:31]([OH:33])[CH3:32])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 1025451-Mercapto-2-propanolHCID 178448620HCID 178448620, compound

Product 1

HCID 178448639HCID 178448639, compoundYield 67.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of Example 81C (400 mg, 1 mmol), 1-mercaptopropan-2-ol (277 mg, 3 mmol) and potassium carbonate (415 mg, 3 mmol) in DMF (10 mL) was heated at 50° C. for 16 hours. The mixture was then poured into water and extracted with ethyl acetate. The acetate layer was washed with brine, dried with MgSO4, filtered, and concentrated under reduced pressure. Purification by chromatography afforded 320 mg of the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 0.91 (t, J=7.3 Hz, 3H), 1.15-1.24 (m, 3H), 1.27-1.44 (m, 11H), 1.54-1.79 (m, 2H), 2.68-3.07 (m, 2H), 3.76-3.94 (m, 4H), 4.27-4.45 (m, 2H), 4.94 (d, J=4.8 Hz, 1H), 6.83 (s, 1H), 7.42-7.52 (m, 1H), 7.54-7.66 (m, 1H), 8.24 (d, J=1.6 Hz, 1H). MS (DCI/NH3) m/z 472 (M+H)+. Anal. calculated for C23H32F3N3O2S: C, 58.58 H, 6.84 N, 8.91. Found: C, 58.57 H, 6.96 N, 8.77.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe acetate layer was washed with brine
  3. dry with materialdried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customPurification by chromatography

Sources & evidence

ORD record
ord-bd0f95a88b1f478987cf52a4656330db
Source dataset
uspto-grants-2012_05
Patent number
US08188135B2

Reaction notes

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