Pyridine → HCID 10186219, compound

HRID 1836192Notes

Reaction equation

HRID 1836192 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]([CH3:31])([CH3:30])[CH2:10][C:11]([OH:29])([C:25]([F:28])([F:27])[F:26])[C:12]([NH:14][C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[C:20](=[O:21])[O:19][CH2:18]2)=[O:13].N1C=CC=CC=1.[S:38](Cl)([CH3:41])(=[O:40])=[O:39]>C(OCC)(=O)C>[F:8][C:5]1[CH:6]=[CH:7][C:2]([NH:1][S:38]([CH3:41])(=[O:40])=[O:39])=[C:3]([C:9]([CH3:31])([CH3:30])[CH2:10][C:11]([OH:29])([C:25]([F:28])([F:27])[F:26])[C:12]([NH:14][C:15]2[CH:16]=[C:17]3[C:22](=[CH:23][CH:24]=2)[C:20](=[O:21])[O:19][CH2:18]3)=[O:13])[CH:4]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 10114149HCID 10114149, compound

Product 1

HCID 10186219HCID 10186219, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

17.7 mg of 5-[4-(2-amino-5-fluorophenyl)-2-hydroxy-4-methyl-2-trifluoromethylvaleroylamino]-phthalide, 0.4 ml of pyridine and 0.078 ml of mesyl chloride are stirred for 17 hours at room temperature, mixed with ethyl acetate, and washed three times with 1N hydrochloric acid. The ethyl acetate solution is dried and concentrated by evaporation. After chromatography on silica gel with ethyl acetate/hexane (1:1), 11 mg of 5-[4-(5-fluoro-2-mesylaminophenyl)-2-hydroxy-4-methyl-2-trifluoromethylvaleroyl-amino]-phthalide is obtained, flash point 218° C.

Workup

  1. washwashed three times with 1N hydrochloric acid
  2. dry with materialThe ethyl acetate solution is dried
  3. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-a47bbd17719e430ea9b6c361058590d5
Source dataset
uspto-grants-2004_08
Patent number
US06777409B2

Reaction notes

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