Methanol → HCID 21883916, compound

HRID 722239Notes

Reaction equation

HRID 722239 reaction equation
[Cl:1][C:2]1[CH:30]=[C:29]([F:31])[C:28]([F:32])=[CH:27][C:3]=1[C:4]([NH:6][C:7](=[O:26])[NH:8][C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=1[N:16]1[CH2:21][CH2:20][CH:19]([C:22]([O:24]C)=[O:23])[CH2:18][CH2:17]1)=[O:5].[OH-].[Li+].O.CO>C1COCC1>[Cl:1][C:2]1[CH:30]=[C:29]([F:31])[C:28]([F:32])=[CH:27][C:3]=1[C:4]([NH:6][C:7](=[O:26])[NH:8][C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=1[N:16]1[CH2:17][CH2:18][CH:19]([C:22]([OH:24])=[O:23])[CH2:20][CH2:21]1)=[O:5]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 3939Lithium HydroxideHCID 21883923HCID 21883923, compound

Product 1

HCID 21883916HCID 21883916, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The mixture consisting of 90 mg of methyl 1-{2-[3-(2-chloro-4,5-difluoro-benzoyl)ureido]-4-chlorophenyl}piperidine-4-carboxylate (Ex.15), 9.6 mg of lithium hydroxide, 3 ml of water, 3 ml of methanol and 3 ml of THF is allowed to stand at room temperature for 36 hours. The volatile fractions are removed at RT under reduced pressure and the remainder is adjusted to pH=4 using 2N hydrochloric acid. The precipitate formed is filtered off with suction and purified by column chromatography (silica gel, solvent: methylene chloride:methanol=9:1).

Workup

  1. customThe volatile fractions are removed at RT under reduced pressure
  2. customThe precipitate formed
  3. filtrationis filtered off with suction
  4. custompurified by column chromatography (silica gel, solvent: methylene chloride:methanol=9:1)

Sources & evidence

ORD record
ord-94a81aca3c9f423382170f9182fc023a
Source dataset
uspto-grants-2006_11
Patent number
US07138414B2

Reaction notes

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