Pyridine → HCID 135927746, compound

HRID 2241171Notes

Reaction equation

HRID 2241171 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:31][CH3:32])=[C:6]([S:8]([NH:11][C:12]2[CH:13]=[C:14]([CH:28]=[CH:29][CH:30]=2)[C:15]([NH:17][C:18]2[CH:23]=[CH:22][C:21]([C:24](=[NH:27])[NH:25][OH:26])=[CH:20][CH:19]=2)=[O:16])(=[O:10])=[O:9])[CH:7]=1.N1C=CC=CC=1.C(C(CCCC)[CH2:42][O:43]C(Cl)=O)C>CN(C)C=O.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:31][CH3:32])=[C:6]([S:8]([NH:11][C:12]2[CH:13]=[C:14]([CH:28]=[CH:29][CH:30]=2)[C:15]([NH:17][C:18]2[CH:19]=[CH:20][C:21]([C:24]3[NH:27][C:42](=[O:43])[O:26][N:25]=3)=[CH:22][CH:23]=2)=[O:16])(=[O:10])=[O:9])[CH:7]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 627832-Ethylhexyl chloroformateHCID 1784907253-(5-chloro-2-methoxy-benzenesulfonylamino)-N-[4-(N-hydroxycarbamimidoyl)-phenyl]-benzamide

Product 1

HCID 135927746HCID 135927746, compoundYield 76.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 3-(5-chloro-2-methoxy-benzenesulfonylamino)-N-[4-(N-hydroxycarbamimidoyl)-phenyl]-benzamide (145 mg, 0.30 mmol) in dimethylformamide (2.0 ml) was treated with pyridine (26 mg, 1.08 equiv.) and cooled to 0° C. Chloroformic acid 2-ethylhexyl ester (59 mg, 0.30 mmol, 1 equiv.) in DMF (0.1 ml) was added dropwise. The mixture was stirred at 0° C. for 30 min, then diluted with water and extracted with ethyl acetate. The combined organic phases were dried over sodium sulfate and evaporated. The residue was suspended in xylene and the mixture was stirred at 100° C. for 1 h and then at 145° C. for 1 h. After cooling to room temperature, the precipitated solid was filtered, washing with xylene, and dried under high vacuum to yield the title compound (115 mg, 75%) as a white solid, MS (ISP): m/e=499.0 (M−H).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined organic phases were dried over sodium sulfate
  3. customevaporated
  4. stirringthe mixture was stirred at 100° C. for 1 h
  5. waitat 145° C. for 1 h
  6. temperatureAfter cooling to room temperature
  7. filtrationthe precipitated solid was filtered
  8. washwashing with xylene
  9. customdried under high vacuum

Sources & evidence

ORD record
ord-fae37e0334634b4094a9bc05c76e99a2
Source dataset
uspto-grants-2010_05
Patent number
US07723538B2

Reaction notes

Loading…