Benzyl Alcohol → HCID 57678832, compound

HRID 491843Notes

Reaction equation

HRID 491843 reaction equation
[CH2:1]([C:3]1[N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:6]=[CH:5][C:4]=1[C:14]1[N:15]=[CH:16][N:17](C2C=C(C=CC=2C)C(O)=O)[CH:18]=1)[CH3:2].C([C:31]1[NH:35]N=CC=1)C.C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:43])=CC=1.CCN(CC)CC.[CH2:60]([OH:67])[C:61]1[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=1.[C:68]1([CH3:74])[CH:73]=[CH:72][CH:71]=[CH:70][CH:69]=1>>[CH2:60]([O:67][C:31](=[O:43])[NH:35][C:71]1[CH:72]=[CH:73][C:68]([CH3:74])=[C:69]([N:17]2[CH:18]=[C:14]([C:4]3[CH:5]=[N:6][N:7]([C:8]4[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=4)[C:3]=3[CH2:1][CH3:2])[N:15]=[CH:16]2)[CH:70]=1)[C:61]1[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=1

Participants

7

Reactant 6

HCID 244Benzyl AlcoholHCID 1140TolueneHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 4984593-ethyl-1H-pyrazoleHCID 21097290HCID 21097290, compound

Product 1

HCID 57678832HCID 57678832, compoundYield 70%

Procedure

3-[4-(5-Ethyl-1-phenyl-1H-pyrazol-4-yl)-imidazol-1-yl]-4-methyl-benzoic acid (prepared by hydrolysis of the methyl ester which was prepared by the method described in Example 2, using the 5-ethylpyrazole intermediate) (780 mg, 2.09 mmol), DPPA (0.52 mL, 2.4 mmol), and Et3N (0.37 mL, 2.7 mmol) were suspended in dry toluene (10 mL) under N2 and stirred for 1 h after which time a clear solution had formed. The reaction mixture was placed into a 100° C. pre-heated oil bath and stirred under N2 for 75 min. Then, benzyl alcohol (1 mL) was added and the reaction stirred at 110° C. for 6 h. The reaction was cooled, concentrated, and purified by chromatography (0 to 75% EtOAc in hexanes) to give the {3-[4-(5-ethyl-1-phenyl-1H-pyrazol-4-yl)-imidazol-1-yl]-4-methyl-phenyl}-carbamic acid benzyl ester as a white foam (695 mg, 70%).

Workup

  1. customwas prepared by the method
  2. customhad formed
  3. customwas placed into a 100° C.
  4. temperaturepre-heated oil bath
  5. stirringstirred under N2 for 75 min
  6. stirringthe reaction stirred at 110° C. for 6 h
  7. temperatureThe reaction was cooled
  8. concentrationconcentrated
  9. custompurified by chromatography (0 to 75% EtOAc in hexanes)

Sources & evidence

ORD record
ord-6885162583484c118e58279146a6e447
Source dataset
uspto-grants-2009_05
Patent number
US07531560B2

Reaction notes

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