Lithium Hydroxide → HCID 10455140, compound

HRID 2111983Notes

Reaction equation

HRID 2111983 reaction equation
[OH-].[Li+].[F:3][C:4]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:5]=1[NH:11][C:12]([NH:14][CH2:15][CH2:16][C:17]1[CH:34]=[CH:33][C:20]([O:21][CH2:22][C:23]2[CH:32]=[CH:31][CH:30]=[CH:29][C:24]=2[C:25]([O:27]C)=[O:26])=[CH:19][CH:18]=1)=[O:13]>O.C1COCC1>[F:3][C:4]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:5]=1[NH:11][C:12]([NH:14][CH2:15][CH2:16][C:17]1[CH:34]=[CH:33][C:20]([O:21][CH2:22][C:23]2[CH:32]=[CH:31][CH:30]=[CH:29][C:24]=2[C:25]([OH:27])=[O:26])=[CH:19][CH:18]=1)=[O:13]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 68871852HCID 68871852, compound

Product 1

HCID 10455140HCID 10455140, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide (3.7 mg, 0.154 mmol) in water (1 ml) was added into methyl 2-({4-[2-({[(2,4-difluorophenyl)amino]carbonyl}amino)ethyl]phenoxy}methyl)benzoate (34 mg, 0.077 mmol) dissolved in THF (2 ml). The mixture was then irradiated in a microwave oven (Smith Synthesizer) at 150° C. for 7 minutes and then evaporated to remove THF. The residue was acidified with 1% hydrochloric acid, pH˜4, and extracted with ethyl acetate (×2). The organic extracts were combined and dried with magnesium sulphate and then evaporated. Chromatography of the residue on a column (ISOLUTE® SI, 1 g/6 ml) using MeOH/DCM (1:99, 2:98, 4:96 and then 10:90) as eluant gave 18 mg the desired product, yield 55%.

Workup

  1. customThe mixture was then irradiated in a microwave oven (Smith Synthesizer) at 150° C. for 7 minutes
  2. customevaporated
  3. customto remove THF
  4. extractionextracted with ethyl acetate (×2)
  5. dry with materialdried with magnesium sulphate
  6. customevaporated

Sources & evidence

ORD record
ord-a1bdcb49a8654abfa905205878bb9e8a
Source dataset
uspto-grants-2009_04
Patent number
US07521461B2

Reaction notes

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