Phenyl chloroformate → HCID 59813257, compound

HRID 1925292Notes

Reaction equation

HRID 1925292 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][CH:7]=[C:6]2[O:15][C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][CH:25]=1)[C:22]([NH2:26])=[CH:21][CH:20]=[CH:19]2.CC[N:29]([CH:33](C)C)[CH:30]([CH3:32])[CH3:31].C1([O:42]C(Cl)=O)C=CC=CC=1.C1(N)CC1>C1COCC1>[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:15][C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][CH:25]=1)[C:22]([NH:26][C:33]([NH:29][CH:30]1[CH2:31][CH2:32]1)=[O:42])=[CH:21][CH:20]=[CH:19]2

Participants

6

Reactant 4

HCID 15891Phenyl chloroformateHCID 69828CyclopropylamineHCID 81531DiisopropylethylamineHCID 675202746-(6,7-Dimethoxyquinolin-4-yloxy)naphthalen-1-amine

Product 1

HCID 59813257HCID 59813257, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

6-(6,7-Dimethoxyquinolin-4-yloxy)naphthalen-1-amine (80 mg, 0.231 mmol) was suspended in THF (1 mL), then added Hunig's base (33 mg, 0.254 mmol) and a solution of phenylchloroformate (36 mg, 0.231 mmol) in THF (0.5 mL). The reaction was stirred at RT for 16 h. A solution of cyclopropylamine (26 mg, 0.462 mmol) in THF (0.6 mL) was added to the mixture and the reaction was heated at 50° C. for 4 h. A precipitate formed and was collected on a glass frit, washed with THF then CH2Cl2. The tan solid was purified by preparative thin layer chromatography (8% MeOH in CH2Cl2) to give N-(6-((6,7-bis(methoxy)-4-quinolinyl)oxy)-1-naphthalenyl)-N′-cyclopropylurea as a white solid. MS (ESI, pos. ion) m/z: 430.2 (M+1). Mass Calc'd for C25H23N3O4: 429.47

Workup

  1. temperaturethe reaction was heated at 50° C. for 4 h
  2. customA precipitate formed
  3. customwas collected on a glass frit
  4. washwashed with THF
  5. customThe tan solid was purified by preparative thin layer chromatography (8% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-d1c4748e60a242a5aaef49d4dbef13c7
Source dataset
uspto-grants-2012_05
Patent number
US08178557B2

Reaction notes

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