Methanesulfonamide → HCID 56644154, compound

HRID 512024Notes

Reaction equation

HRID 512024 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([O:8][CH2:9][C:10]2[CH:18]=[CH:17][C:13]([C:14](O)=[O:15])=[CH:12][CH:11]=2)[CH:5]=[N:6][CH:7]=1.[CH3:19][S:20]([NH2:23])(=[O:22])=[O:21].C1CCN2C(=NCCC2)CC1>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([O:8][CH2:9][C:10]2[CH:18]=[CH:17][C:13]([C:14]([NH:23][S:20]([CH3:19])(=[O:22])=[O:21])=[O:15])=[CH:12][CH:11]=2)[CH:5]=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 72879MethanesulfonamideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 64601728HCID 64601728, compound

Product 1

HCID 56644154HCID 56644154, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 4-{[(5-chloropyridin-3-yl)oxy]methyl}benzoic acid (Preparation 17, 0.16 g, 0.60 mmol) in THF (6 mL) was added WSCDI (0.1 g, 0.62 mmol) and the reaction was heated at reflux for 30 minutes. The reaction mixture was cooled to room temperature and methanesulphonamide (0.060 g, 0.64 mmol) and DBU (0.09 g, 0.060 mmol) were added. The reaction mixture was stirred at room temperature for 1 hour and then partitioned between DCM (30 mL) and aqueous hydrochloric acid (1 M, 8 mL). The organic layer was separated and dried over magnesium sulfate and evaporated in vacuo. The resulting crude was triturated with diethyl ether (4 mL) and methanol (1 mL) to afford the title compound as a beige solid (0.053 g, 51%).

Workup

  1. additionwas added WSCDI (0.1 g, 0.62 mmol)
  2. temperaturethe reaction was heated
  3. temperatureat reflux for 30 minutes
  4. custompartitioned between DCM (30 mL) and aqueous hydrochloric acid (1 M, 8 mL)
  5. customThe organic layer was separated
  6. dry with materialdried over magnesium sulfate
  7. customevaporated in vacuo
  8. customThe resulting crude was triturated with diethyl ether (4 mL) and methanol (1 mL)

Sources & evidence

ORD record
ord-24b0fe0adb7042b2a2300bafb30b1bb2
Source dataset
uspto-grants-2015_08
Patent number
US09102621B2

Reaction notes

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