Tetrahydrofurfuryl alcohol → HCID 19699086, compound

HRID 863053Notes

Reaction equation

HRID 863053 reaction equation
[NH2:1][C:2]1[CH:23]=[CH:22][C:5]([C:6]([N:8]2[CH2:14][CH2:13][C:12]3[CH:15]=[N:16][NH:17][C:11]=3[C:10]3[N:18]=[CH:19][CH:20]=[CH:21][C:9]2=3)=[O:7])=[CH:4][CH:3]=1.[C:24]1([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH:29]=[CH:28][C:27](C(Cl)=O)=[CH:26][CH:25]=1.C(N(CC)C(C)C)(C)C.[OH-].[Na+].[O:50]1CCC[CH:51]1CO>ClCCl.O1CCCC1.CO.O1CCCC1>[NH:17]1[C:11]2[C:10]3[N:18]=[CH:19][CH:20]=[CH:21][C:9]=3[N:8]([C:6]([C:5]3[CH:22]=[CH:23][C:2]([NH:1][C:51]([C:38]4[C:33]([C:24]5[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=5)=[CH:34][CH:35]=[CH:36][CH:37]=4)=[O:50])=[CH:3][CH:4]=3)=[O:7])[CH2:14][CH2:13][C:12]=2[CH:15]=[N:16]1

Participants

9

Reactant 5

HCID 7360Tetrahydrofurfuryl alcoholHCID 14798Sodium HydroxideHCID 81531DiisopropylethylamineHCID 841514-Phenylbenzoyl chlorideHCID 19699088HCID 19699088, compound

Product 1

HCID 19699086HCID 19699086, compound

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A mixture of 0.23 g of 6-(4-aminobenzoyl)-1,4,5,6-tetrahydropyrazolo[3,4-d]pyrido[3,2-b]azepine, 0.375 g of 4-[1,1'-biphenyl]carbonyl chloride and 0.224 g of N,N-diisopropylethylamine in 5 ml of dichloromethane and 1 ml of tetrahydrofuran is stirred at room temperature for 6 hours. The solvent is removed and the residue dissolved in 80 ml of chloroform. The solution is washed 2 times each with 1N NaHCO3, H2O, brine and dried (Na2SO4). The solution is filtered through a thin pad of hydrous magnesium silicate and the filter pad washed with ethyl acetate. The filtrate is concentrated to dryness under vacuum. To the residue (0.64 g) in 6 ml of methanol-tetrahydrofuran (1:1) is added 2.0 mmol of 1M NaOH and the mixture stirred at room temperature for 2 hours. To the mixture is added 10 ml of tetrahydrofuran-methanol (1:1) and the mixture stirred for 2 hours. The volatiles are removed under vacuum, H2O added and the mixture acidified with acetic acid. The mixture is extracted with dichloromethane and the extract washed with H2O, brine and dried (Na2SO4). The solvent is removed and the residue heated with hexane (700 ml) and filtered. The insoluble solid is crystallized from CH2Cl2 -hexane to give 0.25 g of white crystals, mp 250°-251° C.

Workup

  1. customThe solvent is removed
  2. dissolutionthe residue dissolved in 80 ml of chloroform
  3. washThe solution is washed 2 times each with 1N NaHCO3, H2O, brine
  4. dry with materialdried (Na2SO4)
  5. filtrationThe solution is filtered through a thin pad of hydrous magnesium silicate
  6. washthe filter pad washed with ethyl acetate
  7. concentrationThe filtrate is concentrated to dryness under vacuum
  8. stirringthe mixture stirred at room temperature for 2 hours
  9. stirringthe mixture stirred for 2 hours
  10. customThe volatiles are removed under vacuum, H2O
  11. additionadded
  12. extractionThe mixture is extracted with dichloromethane
  13. washthe extract washed with H2O, brine
  14. dry with materialdried (Na2SO4)
  15. customThe solvent is removed
  16. temperaturethe residue heated with hexane (700 ml)
  17. filtrationfiltered
  18. customThe insoluble solid is crystallized from CH2Cl2 -hexane

Sources & evidence

ORD record
ord-cd6f60abb6ab476181ebc550e024663f
Source dataset
uspto-grants-1998_02
Patent number
US05719278

Reaction notes

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