Pyridine → HCID 9998971, compound

HRID 1171035Notes

Reaction equation

HRID 1171035 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:15]([NH2:17])=[N:14][CH:13]=[N:12][C:11]=3[O:10][CH:9]=2)=[CH:4][CH:3]=1.N1C=CC=CC=1.[C:24]1([S:30](Cl)(=[O:32])=[O:31])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>ClCCl.O>[NH2:17][C:15]1[C:16]2[C:8]([C:5]3[CH:4]=[CH:3][C:2]([NH:1][S:30]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)(=[O:32])=[O:31])=[CH:7][CH:6]=3)=[CH:9][O:10][C:11]=2[N:12]=[CH:13][N:14]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 7369Benzenesulfonyl chlorideHCID 59794225HCID 59794225, compound

Product 1

HCID 9998971HCID 9998971, compoundYield 64.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A 0° C. suspension of Example 13E (0.05 g, 0.22 mmol) in dichloromethane (4 mL) was treated with pyridine (0.022 mL, 0.26 mmol) and benzenesulfonyl chloride (0.03 mL, 0.23 mmol), stirred at 0° C. for 1 hour, warmed to room temperature, and stirred overnight. The reaction mixture was diluted with water and extracted twice with dichloromethane. The combined extracts were washed with brine, dried (Na2SO4), filtered, and concentrated. The concentrate was triturated with dichloromethane/hexanes to provide 52 mg (64%) of the desired product. MS (ESI(+)) m/e 367 (M+H)+; 1H NMR (DMSO-d6) δ 10.51 (s, 1H), 8.23 (s, 1H), 7.88 (s, 1H), 7.84-7.81 (m, 2H), 7.64-7.54 (m, 3H), 7.38 (d, J=8.5 Hz, 2H), 7.22 (d, J=8.5 Hz, 2H), 6.45 (br s, 2H); Anal. Calcd. for C18H14N4O3S: C, 59.01; H, 3.85; N, 15.29. Found: C, 58.77; H, 3.88; N, 15.18.

Workup

  1. temperaturewarmed to room temperature
  2. stirringstirred overnight
  3. extractionextracted twice with dichloromethane
  4. washThe combined extracts were washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe concentrate was triturated with dichloromethane/hexanes

Sources & evidence

ORD record
ord-0fb936de0d024e419460c7113bb1b478
Source dataset
uspto-grants-2010_11
Patent number
US07829570B2

Reaction notes

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