1-Hydroxybenzotriazole → HCID 21890638, compound

HRID 721623Notes

Reaction equation

HRID 721623 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][N:7]=[C:6]2[O:15][C:16]1[CH:26]=[CH:25][C:19]([O:20][CH2:21][C:22]([OH:24])=O)=[CH:18][CH:17]=1.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.[N:49]1([CH:55]2[CH2:60][CH2:59][NH:58][CH2:57][CH2:56]2)[CH2:54][CH2:53][CH2:52][CH2:51][CH2:50]1.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][N:7]=[C:6]2[O:15][C:16]1[CH:26]=[CH:25][C:19]([O:20][CH2:21][C:22]([N:58]2[CH2:59][CH2:60][CH:55]([N:49]3[CH2:54][CH2:53][CH2:52][CH2:51][CH2:50]3)[CH2:56][CH2:57]2)=[O:24])=[CH:18][CH:17]=1

Participants

8

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 786071,4'-BipiperidineHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 21889996HCID 21889996, compound

Product 1

HCID 21890638HCID 21890638, compoundYield 24%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

2-{4-[(6,7-Dimethoxy-4-quinazolinyl)oxy]phenoxy}acetic acid (100 mg), WSC.HCl (81 mg), and HOBT.H2O (57 mg) were dissolved in chloroform (3 ml) to prepare a solution. 4-Piperidinopiperidine (57 mg) was then added to the solution, and the mixture was stirred at room temperature overnight. A saturated aqueous sodium hydrogencarbonate solution was added to the reaction solution, and the mixture was extracted with chloroform. The extract was washed with saturated brine and was then dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure. The residue was purified by thin-layer chromatography using chloroform/methanol for development. Diethyl ether was added to the purification product, and the precipitated crystal was collected by filtration and was washed to give the title compound (34 mg, yield 24%).

Workup

  1. customto prepare a solution
  2. extractionthe mixture was extracted with chloroform
  3. washThe extract was washed with saturated brine
  4. dry with materialwas then dried over anhydrous sodium sulfate
  5. customThe solvent was removed by distillation under the reduced pressure
  6. customThe residue was purified by thin-layer chromatography
  7. additionDiethyl ether was added to the purification product
  8. filtrationthe precipitated crystal was collected by filtration
  9. washwas washed

Sources & evidence

ORD record
ord-8dbc8a0db9ac48d48f6aecfee4f3c90f
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

Loading…