Benzyl Alcohol → HCID 68420963, compound

HRID 1610148Notes

Reaction equation

HRID 1610148 reaction equation
[F:1][C:2]1[C:10](C(O)=O)=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([C:33]1[CH:38]=[CH:37][CH:36]=[C:35]([F:39])[CH:34]=1)=[N:5][N:6]2[C:14]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C([N:42]([CH2:45]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:54])C=CC=CC=1.[CH2:64]([OH:71])[C:65]1[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=1>C1(C)C=CC=CC=1.O>[CH2:64]([O:71][C:45](=[O:54])[NH:42][C:10]1[C:2]([F:1])=[C:3]2[C:7](=[CH:8][CH:9]=1)[N:6]([C:14]([C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[N:5]=[C:4]2[C:33]1[CH:38]=[CH:37][CH:36]=[C:35]([F:39])[CH:34]=1)[C:65]1[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=1

Participants

7

Reactant 4

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 22261056HCID 22261056, compound

Product 1

HCID 68420963HCID 68420963, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A total of 1.29 g of 4-fluoro-3-(3-fluoro-phenyl)-1-trityl-1H-indazole-5-carboxylic acid obtained in Production Example II-19-a was dissolved in 12.5 ml of toluene. Under stirring at room temperature, 0.38 ml of triethylamine and 0.566 ml of diphenylphosphoryl azide were added, and the mixture was stirred at room temperature for 2 hours and at 120° C. for further 1.5 hours. To the reaction mixture was added 0.776 ml of benzyl alcohol, followed by stirring at 120° C. for 1.5 hours. After cooling to room temperature, the reaction mixture was added with water, and extracted with ethyl acetate. The resulting organic layer was washed with brine, dried over magnesium sulfate and the solvent was evaporated. The residue was purified and separated by silica gel column chromatography (ethyl acetate:hexane=1:5), to give 652 mg of the title compound as an ocher yellow oil.

Workup

  1. stirringthe mixture was stirred at room temperature for 2 hours and at 120° C. for further 1.5 hours
  2. stirringby stirring at 120° C. for 1.5 hours
  3. temperatureAfter cooling to room temperature
  4. extractionextracted with ethyl acetate
  5. washThe resulting organic layer was washed with brine
  6. dry with materialdried over magnesium sulfate
  7. customthe solvent was evaporated
  8. customThe residue was purified
  9. customseparated by silica gel column chromatography (ethyl acetate:hexane=1:5)

Sources & evidence

ORD record
ord-f41dfd7496744a30b651772247d6a3d8
Source dataset
uspto-grants-2006_01
Patent number
US06982274B2

Reaction notes

Loading…