Triphenylphosphine → (4-Tert-butylphenyl)-{4-[6-methoxy-7-(4-piperidinylmethoxy)-4-quinolyloxy]phenyl}amine

HRID 1727861Notes

Reaction equation

HRID 1727861 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][C:19]3[C:28]4[C:23](=[CH:24][C:25]([OH:31])=[C:26]([O:29][CH3:30])[CH:27]=4)[N:22]=[CH:21][CH:20]=3)=[CH:14][CH:13]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(C1C=CC(NC2C=CC(OC3C4C(=CC(OCCCCl)=C(OC)C=4)N=CC=3)=CC=2)=CC=1)(C)(C)C.C(OC([N:74]1[CH2:79][CH2:78][CH:77]([CH2:80]O)[CH2:76][CH2:75]1)=O)(C)(C)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1.C(Cl)(Cl)Cl.CC(C)=O.C(OCC)(=O)C.O>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][C:19]3[C:28]4[C:23](=[CH:24][C:25]([O:31][CH2:80][CH:77]5[CH2:78][CH2:79][NH:74][CH2:75][CH2:76]5)=[C:26]([O:29][CH3:30])[CH:27]=4)[N:22]=[CH:21][CH:20]=3)=[CH:14][CH:13]=2)=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

10

Reactant 5

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 2764081Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate2×HCID 57567448(4-Tert-butylphenyl)-{4-[7-(3-chloropropoxy)-6-methoxy-4-quinolyloxy]phenyl}amineHCID 1357802514-[4-(4-Tert-butylphenylamino)phenoxy]-6-methoxyquinolin-7-ol2×

Product 1

HCID 69055371(4-Tert-butylphenyl)-{4-[6-methoxy-7-(4-piperidinylmethoxy)-4-quinolyloxy]phenyl}amineYield 86%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 15930782Chloroform acetoneSolvent

Procedure

(4-Tert-butylphenyl)-[4-(6-methoxy-7-hydroxy-4-quinolyloxy)-phenyl]amine (compound 21) (0.8 g) (starting compound A), tert-butyl-4-(hydroxymethyl)-1-piperidine carboxylate (0.59 g) (starting compound B), and triphenylphosphine (0.85 g) were dissolved in tetrahydrofuran (25 ml), and the solution was stirred at room temperature for 20 min. Under ice cooling, 40% diethyl azodicarboxylate (1.5 ml) was added to the reaction solution, and the mixture was stirred at room temperature overnight. Water and ethyl acetate were added to the reaction solution. The mixture was extracted with ethyl acetate, and the extract was washed with saturated brine and was dried over sodium sulfate. The solvent was removed by evaporation under the reduced pressure. The crude was dissolved in a 30% trifluoroacetic acid/chloroform solution (15 ml), and the solution was stirred at room temperature for 30 min. The solvent was removed by evaporation under the reduced pressure, and the residue was then purified by chromatography on silica get using chloroform/acetone for development to give (4-tert-butylphenyl)-{4-[6-methoxy-7-(4-piperidinylmethoxy)-4-quinolyloxy]phenyl}amine (0.84 g, yield 86%).

Workup

  1. stirringthe mixture was stirred at room temperature overnight
  2. extractionThe mixture was extracted with ethyl acetate
  3. washthe extract was washed with saturated brine
  4. dry with materialwas dried over sodium sulfate
  5. customThe solvent was removed by evaporation under the reduced pressure
  6. dissolutionThe crude was dissolved in a 30% trifluoroacetic acid/chloroform solution (15 ml)
  7. stirringthe solution was stirred at room temperature for 30 min
  8. customThe solvent was removed by evaporation under the reduced pressure
  9. customthe residue was then purified by chromatography on silica
  10. customget

Sources & evidence

ORD record
ord-4424698cf813427fbc29bde0de2c1552
Source dataset
uspto-grants-2009_02
Patent number
US07495104B2

Reaction notes

Loading…