3-Methoxyaniline → HCID 21890236, compound

HRID 721618Notes

Reaction equation

HRID 721618 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](O)=[O:23])=[CH:18][CH:17]=1.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.[CH3:49][O:50][C:51]1[CH:56]=[CH:55][CH:54]=[C:53]([NH2:57])[CH:52]=1.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl.O>[CH3:49][O:50][C:51]1[CH:52]=[C:53]([NH:57][C:22](=[O:23])[CH2:21][O:20][C:19]2[CH:18]=[CH:17][C:16]([O:15][C:6]3[C:5]4[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=4)[N:9]=[CH:8][N:7]=3)=[CH:26][CH:25]=2)[CH:54]=[CH:55][CH:56]=1

Participants

8

Reactant 5

HCID 108243-MethoxyanilineHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 21889996HCID 21889996, compound

Product 1

HCID 21890236HCID 21890236, compoundYield 15%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

2-{4-[(6,7-Dimethoxy-4-quinazolinyl)oxy]phenoxy}-acetic acid (150 mg), WSC.HCl (122 mg), and HOBT.H2O (86 mg) were dissolved in chloroform (5 ml) to prepare a solution. m-Anisidine (63 mg) was then added to the solution, and the mixture was stirred at room temperature for 4 hr. A saturated aqueous sodium hydrogencarbonate solution was added to the reaction solution, and the mixture was extracted with chloroform. The chloroform layer was washed with 1 N hydrochloric acid, water, and 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 (29 mg, yield 15%).

Workup

  1. customto prepare a solution
  2. extractionthe mixture was extracted with chloroform
  3. washThe chloroform layer was washed with 1 N hydrochloric acid, water, and 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-54b1001a04a04341a11fdd6deaec04d6
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

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