HCID 59140413, compound → HCID 86637791, compound

HRID 216407Notes

Reaction equation

HRID 216407 reaction equation
C([Li])CCC.[S:6]1[CH2:11][CH2:10][CH2:9][S:8][CH:7]1[C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=2)=[CH:14][CH:13]=1.[CH3:24][C:25]([CH3:41])([CH3:40])[CH2:26][C:27]1[N:28]=[C:29]([CH:38]=[O:39])[N:30]([S:32]([N:35]([CH3:37])[CH3:36])(=[O:34])=[O:33])[CH:31]=1>O1CCCC1>[CH3:24][C:25]([CH3:41])([CH3:40])[CH2:26][C:27]1[N:28]=[C:29]([CH:38]([OH:39])[C:7]2([C:12]3[CH:13]=[CH:14][C:15]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=4)=[CH:16][CH:17]=3)[S:8][CH2:9][CH2:10][CH2:11][S:6]2)[N:30]([S:32]([N:35]([CH3:36])[CH3:37])(=[O:33])=[O:34])[CH:31]=1

Participants

5

Reactant 3

HCID 59140413HCID 59140413, compoundHCID 86637792HCID 86637792, compoundHCID 178418339Butyllithium

Product 1

HCID 86637791HCID 86637791, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

n-Butyllithium (2.5 M in hexane) (0.14 mL, 0.17 mol) was added to a −78° C. solution of 2-[4-(1,3-dithian-2-yl)phenyl]pyridine (50 mg, 0.18 mmol) in tetrahydrofuran (3 mL). After stirring at 0° C. for 10 min, the reaction mixture was re-cooled to −78° C. and a solution of 4-(2,2-dimethylpropyl)-2-formyl-N,N-dimethyl-1H-imidazole-1-sulfonamide (100 mg, 0.37 mmol) in tetrahydrofuran (1 mL) was added. After stirring at −78° C. for 5 min then at ambient temperature for a further 10 min, the reaction mixture was quenched with water and extracted with methylene chloride. The combined organic extracts were dried (magnesium sulfate) and concentrated in vacuo. Preparatory plate chromatography eluting with 50% ethyl acetate/hexane afforded 4-(2,2-dimethylpropyl)-2-{hydroxy[2-(4-pyridin-2-ylphenyl)-1,3-dithian-2-yl]methyl}-N,N-dimethyl-1H-imidazole-1-sulfonamide. LCMS: 547 (M+H).

Workup

  1. temperaturethe reaction mixture was re-cooled to −78° C.
  2. stirringAfter stirring at −78° C. for 5 min
  3. waitat ambient temperature for a further 10 min
  4. customthe reaction mixture was quenched with water
  5. extractionextracted with methylene chloride
  6. dry with materialThe combined organic extracts were dried (magnesium sulfate)
  7. concentrationconcentrated in vacuo
  8. washPreparatory plate chromatography eluting with 50% ethyl acetate/hexane

Sources & evidence

ORD record
ord-ffb2c3f797204793a0132a387738c74c
Source dataset
uspto-grants-2012_06
Patent number
US08193228B2

Reaction notes

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