Toluene → N-[3-(hydroxymethyl)phenyl]-4-(3-phenyl-1,2,4-thiadiazol-5-yl)piperazine-1-carboxamide

HRID 2262974Notes

Reaction equation

HRID 2262974 reaction equation
[C:1]1([C:7]2[N:11]=[C:10]([N:12]3[CH2:17][CH2:16][N:15]([C:18]([NH:20][C:21]4[CH:22]=[C:23]([CH:28]=[CH:29][CH:30]=4)[C:24](OC)=[O:25])=[O:19])[CH2:14][CH2:13]3)[S:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].C([Al+]CC(C)C)C(C)C.C1(C)C=CC=CC=1.[Cl-].[NH4+]>O1CCCC1>[OH:25][CH2:24][C:23]1[CH:22]=[C:21]([NH:20][C:18]([N:15]2[CH2:16][CH2:17][N:12]([C:10]3[S:9][N:8]=[C:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[N:11]=3)[CH2:13][CH2:14]2)=[O:19])[CH:30]=[CH:29][CH:28]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 25517Ammonium ChlorideHCID 21225700DiisobutylaluminumhydrideHCID 68776379Methyl 3-({[4-(3-phenyl-1,2,4-thiadiazol-5-yl)piperazin-1-yl]carbonyl}amino)benzoate

Product 1

HCID 68778002N-[3-(hydroxymethyl)phenyl]-4-(3-phenyl-1,2,4-thiadiazol-5-yl)piperazine-1-carboxamideYield 15%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under a nitrogen gas stream, to a solution of methyl 3-({[4-(3-phenyl-1,2,4-thiadiazol-5-yl)piperazin-1-yl]carbonyl}amino)benzoate (300 mg, 0.710 mmol) in tetrahydrofuran (7.0 ml) was added, under ice-cooling, a 1.5 M solution of diisobutylaluminum hydride in toluene (4.7 ml, 7.10 mmol), and the mixture was stirred at room temperature for 2 hours. An aqueous saturated ammonium chloride solution was poured to the reaction mixture, and the resulting solution was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1) and recrystallized from a mixed solvent of hexane and tetrahydrofuran to give 42 mg (15.0%) of the desired product as a solid.

Workup

  1. temperaturecooling
  2. extractionthe resulting solution was extracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1)
  7. customrecrystallized from a mixed solvent of hexane and tetrahydrofuran

Sources & evidence

ORD record
ord-59890a2f80bd415a9d3c9a5ef19f15a8
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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