Pyridine → HCID 58508703, compound

HRID 454626Notes

Reaction equation

HRID 454626 reaction equation
N1C=CC=CC=1.[CH3:7][S:8](Cl)(=[O:10])=[O:9].Cl.[OH:13][C:14]1[CH:37]=[CH:36][C:35]([O:38][CH:39]2[CH2:44][CH2:43][NH:42][CH2:41][CH2:40]2)=[CH:34][C:15]=1[C:16]([NH:18][C:19]1[CH:27]=[C:26]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:25]=[CH:24][C:20]=1[C:21]([OH:23])=[O:22])=[O:17]>C(Cl)Cl>[OH:13][C:14]1[CH:37]=[CH:36][C:35]([O:38][CH:39]2[CH2:40][CH2:41][N:42]([S:8]([CH3:7])(=[O:10])=[O:9])[CH2:43][CH2:44]2)=[CH:34][C:15]=1[C:16]([NH:18][C:19]1[CH:27]=[C:26]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:25]=[CH:24][C:20]=1[C:21]([OH:23])=[O:22])=[O:17]

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 66991248HCID 66991248, compound

Product 1

HCID 58508703HCID 58508703, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under ice-cooling, pyridine (0.5 mL) and methanesulfonyl chloride (9.9 μL) were sequentially added to a methylene chloride (1 mL) suspension of 2-(2-hydroxy-5-(piperidin-4-yloxy)benzamido)-4-phenylbenzoic acid hydrochloride (0.030 g), followed by stirring at room temperature for 5 hours and 30 minutes. The solvent was evaporated under reduced pressure, and methanol (0.5 mL) and a 2 mol/L aqueous solution of sodium hydroxide (0.5 mL) were added to the residue, followed by stirring at 70° C. for 45 minutes. The reaction mixture was cooled to room temperature, and then 1 mol/L hydrochloric acid (5 mL) was added thereto. The solid substance was collected by filtration and the obtained solid substance was purified by silica gel column chromatography [Kanto Chemical Co., Inc., silica gel 60 (spherical), eluent: chloroform] to obtain 8.0 mg of 2-(2-hydroxy-5-(1-(methylsulfonyl)piperidin-4-yloxy)benzamido)-4-phenylbenzoic acid as a white solid.

Workup

  1. temperatureUnder ice-cooling
  2. customThe solvent was evaporated under reduced pressure, and methanol (0.5 mL)
  3. additiona 2 mol/L aqueous solution of sodium hydroxide (0.5 mL) were added to the residue
  4. stirringby stirring at 70° C. for 45 minutes
  5. temperatureThe reaction mixture was cooled to room temperature
  6. addition1 mol/L hydrochloric acid (5 mL) was added
  7. filtrationThe solid substance was collected by filtration
  8. customthe obtained solid substance was purified by silica gel column chromatography [Kanto Chemical Co., Inc., silica gel 60 (spherical), eluent: chloroform]

Sources & evidence

ORD record
ord-8fd2f7977d4f44e582654d3ca0818758
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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