Dichloromethane → HCID 57736542, compound

HRID 1641736Notes

Reaction equation

HRID 1641736 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[CH:9]([S:23]([C:26]1[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=1)(=[O:25])=[O:24])[C:10]1[C:11]([CH3:22])=[CH:12][C:13]([C:16]([NH:18][CH2:19][CH2:20]O)=[O:17])=[N:14][CH:15]=1.C(Cl)[Cl:34]>S(Cl)(Cl)=O>[Cl:34][CH2:20][CH2:19][NH:18][C:16]([C:13]1[CH:12]=[C:11]([CH3:22])[C:10]([CH:9]([C:3]2[CH:4]=[C:5]([F:8])[CH:6]=[CH:7][C:2]=2[F:1])[S:23]([C:26]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=2)(=[O:25])=[O:24])=[CH:15][N:14]=1)=[O:17]

Participants

4

Reactant 2

HCID 6344DichloromethaneHCID 57736474HCID 57736474, compound

Product 1

HCID 57736542HCID 57736542, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent2×

Procedure

To a solution of 5-[(2,5-difluorophenyl)[(4-fluorophenyl)sulfonyl]methyl]-N-(2-hydroxyethyl)-4-methylpyridine-2-carboxamide (120 mg, 0.258 mmol) obtained in Example 17 in methylene chloride (5 ml), thionyl chloride (100 μl) was added, and the mixture was stirred for 4 hours at room temperature. Thionyl chloride (100 μl) was added to the reaction solution, and the mixture was stirred for 1.5 hours at room temperature. The reaction solution was concentrated under reduced pressure, subsequently saturated aqueous sodium hydrogencarbonate was added thereto, and the mixture was extracted with methylene chloride. The organic layer was dried over anhydrous sodium sulfate and filtered, and then the filtrate was concentrated under reduced pressure. The resulting concentration residue was subjected to silica gel column chromatography, and the fraction obtained from an elution with 35% ethyl acetate/hexane was concentrated under reduced pressure, to obtain the title compound (102 mg, 0.211 mmol, 82%) as a white solid.

Workup

  1. stirringthe mixture was stirred for 1.5 hours at room temperature
  2. concentrationThe reaction solution was concentrated under reduced pressure, subsequently saturated aqueous sodium hydrogencarbonate
  3. additionwas added
  4. extractionthe mixture was extracted with methylene chloride
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. concentrationThe resulting concentration residue
  9. customthe fraction obtained from an elution with 35% ethyl acetate/hexane
  10. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-63ffa2f3861b477cbca277ca21a684d9
Source dataset
uspto-grants-2012_02
Patent number
US08114886B2

Reaction notes

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