Tetrahydrofuran → HCID 19699087, compound

HRID 863054Notes

Reaction equation

HRID 863054 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])=[C:4]([Cl:24])[CH:3]=1.[C:25]1([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH:30]=[CH:29][C:28](C(Cl)=O)=[CH:27][CH:26]=1.C(N(CC)C(C)C)(C)C.[OH-].[Na+].[O:51]1CCC[CH2:52]1>ClCCl.CO>[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:52]([C:39]4[C:34]([C:25]5[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=5)=[CH:35][CH:36]=[CH:37][CH:38]=4)=[O:51])=[CH:3][C:4]=3[Cl:24])=[O:7])[CH2:14][CH2:13][C:12]=2[CH:15]=[N:16]1

Participants

8

Reactant 5

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 81531DiisopropylethylamineHCID 841514-Phenylbenzoyl chlorideHCID 19699102HCID 19699102, compound

Product 1

HCID 19699087HCID 19699087, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 0.3 g of 6-(4-amino-2-chlorobenzoyl)-1,4,5,6-tetrahydropyrazolo[3,4-d]pyrido[3,2-b]azepine, 0.52 g of 4-[1,1'-biphenyl]carbonyl chloride and 0.5 g of N,N-diisopropylethylamine in 10 ml of dichloromethane and 2 ml of tetrahydrofuran is stirred at room temperature for 24 hours. The solvent is removed and to the residue is added 10 ml of methanol and 5 mmol of 1N NaOH. The mixture is stirred overnight, concentrated under vacuum and diluted with water. The mixture is extracted with dichloromethane and the extract washed with 2N NaHCO3, H2O, brine and dried (Na2 SO4). The solvent is removed under vacuum to give the product as a solid (glass), m.p. 181°-192° C.

Workup

  1. customThe solvent is removed and to the residue
  2. stirringThe mixture is stirred overnight
  3. concentrationconcentrated under vacuum
  4. additiondiluted with water
  5. extractionThe mixture is extracted with dichloromethane
  6. washthe extract washed with 2N NaHCO3, H2O, brine
  7. customdried (Na2 SO4)
  8. customThe solvent is removed under vacuum

Sources & evidence

ORD record
ord-8abf526acb2e433e9b323783af018510
Source dataset
uspto-grants-1998_02
Patent number
US05719278

Reaction notes

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