Methanol → HCID 67508061, compound

HRID 2172875Notes

Reaction equation

HRID 2172875 reaction equation
[Cl:1][C:2]1[C:3]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)=[N:4][C:5]([N:8]2[CH2:13][CH2:12][N:11]([S:14]([CH:17]=[CH2:18])(=[O:16])=[O:15])[CH2:10][CH2:9]2)=[CH:6][CH:7]=1.[CH3:25][OH:26]>CCCCCCC.O>[Cl:1][C:2]1[C:3]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)=[N:4][C:5]([N:8]2[CH2:9][CH2:10][N:11]([S:14]([CH2:17][CH2:18][O:26][CH3:25])(=[O:16])=[O:15])[CH2:12][CH2:13]2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 887MethanolHCID 67508055HCID 67508055, compound

Product 1

HCID 67508061HCID 67508061, compoundYield 39%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8900HeptaneSolvent

Conditions

Temperature
0 °C

Procedure

To a 0° C. solution of 3-chloro-6-(4-(vinylsulfonyl)piperazin-1-yl)-2,2′-bipyridine (68 mg, 0.190 mL) in methanol (1.8 mL), Na metal (47.5 mg, 2.05 mmol) washed in heptane was added and stirred for 15 min at 0° C. The reaction mixture was heated to 50° C. and stirred for 2 h and was cooled to RT, diluted with H2O (20 mL), extracted with ethyl acetate (3×20 mL). The combined organic layer was washed with brine (15 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure and purified by column chromatography (30 to 75% ethyl acetate/heptane) to obtain pure product (29 mg, 39% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 8.65 (d, J=4.80 Hz, 1 H) 7.92 (td, J=7.71, 1.77 Hz, 1 H) 7.75 (d, J=9.09 Hz, 1 H) 7.69 (d, J=7.83 Hz, 1 H) 7.44 (ddd, J=7.52, 4.86, 1.01 Hz, 1 H) 7.00 (d, J=8.84 Hz, 1 H) 3.57-3.70 (m, 8 H) 3.35 (t, J=5.94 Hz, 2 H) 3.30 (s, 3 H) 3.22-3.27 (m, 2 H). LCMS (M+H)+: 397.0.

Workup

  1. additionwas added
  2. temperatureThe reaction mixture was heated to 50° C.
  3. stirringstirred for 2 h
  4. temperaturewas cooled to RT
  5. extractionextracted with ethyl acetate (3×20 mL)
  6. washThe combined organic layer was washed with brine (15 mL)
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. custompurified by column chromatography (30 to 75% ethyl acetate/heptane)

Sources & evidence

ORD record
ord-fda03e1711ba4a57af7dc80443546417
Source dataset
uspto-grants-2015_06
Patent number
US09056865B2

Reaction notes

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