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Triethylamine → 1-[4-(6,7-Dimethoxy-quinolin-4-yloxy)-phenyl]-3-(3,3-dimethyl-butyl)-urea

HRID 1727876
Notes
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Reaction equation

HRID 1727876 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]=[C:8](OC1C=CC(N)=CC=1)[CH:7]=[CH:6]2.[CH2:23](N(CC)CC)C.ClC(Cl)(OC(=O)OC(Cl)(Cl)Cl)Cl.C(O[C:47]([N:49]1[CH2:54][CH2:53][CH:52]([CH2:55]O)[CH2:51]C1)=[O:48])(C)(C)C.C(C1C=CC([NH:67][C:68]2[CH:73]=[CH:72][C:71]([O:74]C3C4C(=CC(OCCCCl)=C(OC)C=4)N=CC=3)=[CH:70][CH:69]=2)=CC=1)(C)(C)C>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][CH:7]=[C:6]2[O:74][C:71]1[CH:72]=[CH:73][C:68]([NH:67][C:47]([NH:49][CH2:54][CH2:53][C:52]([CH3:51])([CH3:55])[CH3:23])=[O:48])=[CH:69][CH:70]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 2764081Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate2×HCID 57567448(4-Tert-butylphenyl)-{4-[7-(3-chloropropoxy)-6-methoxy-4-quinolyloxy]phenyl}amine2×HCID 666663974-[(6,7-Dimethoxy-quinolyl)oxy]aniline

Product 1

HCID 23022665
1-[4-(6,7-Dimethoxy-quinolin-4-yloxy)-phenyl]-3-(3,3-dimethyl-butyl)-urea
Yield 59%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent2×

Procedure

4-[(6,7-Dimethoxy-quinolyl)oxy]aniline (2 g) was dissolved in chloroform (100 ml) (starting compound A) to prepare a solution. Triethylamine (2 ml) was added to the solution. A solution of triphosgene (1 g) in chloroform (4 ml) was added dropwise thereto, and the mixture was stirred at room temperature for 30 min. 3,3-Dimethylbutylamine (750 mg) (starting compound B) was added thereto, and the mixture was stirred at room temperature for 5 hr. Water and chloroform were added to the reaction solution, and the mixture was extracted with chloroform. The extract was washed with saturated brine and was dried over sodium sulfate. The solvent was then removed by evaporation under the reduced pressure. The crude thus obtained was purified by chromatography on silica gel using chloroform/acetone for development to give the title compound (1.70 g, yield 59%).

Workup

  1. customto prepare a solution
  2. stirringthe mixture was stirred at room temperature for 5 hr
  3. extractionthe mixture was extracted with chloroform
  4. washThe extract was washed with saturated brine
  5. dry with materialwas dried over sodium sulfate
  6. customThe solvent was then removed by evaporation under the reduced pressure
  7. customThe crude thus obtained
  8. customwas purified by chromatography on silica gel

Sources & evidence

ORD record
ord-cb5b73f9c86544589392e2d3c0d4cb98
Source dataset
uspto-grants-2009_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07495104B2

Reaction notes

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