1,2-Dichloroethane → HCID 59813846, compound

HRID 1925348Notes

Reaction equation

HRID 1925348 reaction equation
[C:1](C1NC=CN=1)(C1NC=CN=1)=S.[CH3:13][O:14][C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][C:24]=1[O:25][CH3:26])[N:21]=[CH:20][CH:19]=[C:18]2[O:27][C:28]1[CH:29]=[C:30]2[C:35](=[CH:36][CH:37]=1)[C:34]([NH2:38])=[CH:33][CH:32]=[CH:31]2.[NH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=1[OH:46].C(Cl)CCl>C(Cl)Cl.CC#N>[CH3:13][O:14][C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][C:24]=1[O:25][CH3:26])[N:21]=[CH:20][CH:19]=[C:18]2[O:27][C:28]1[CH:29]=[C:30]2[C:35](=[CH:36][CH:37]=1)[C:34]([NH:38][C:1]1[O:46][C:41]3[CH:42]=[CH:43][CH:44]=[CH:45][C:40]=3[N:39]=1)=[CH:33][CH:32]=[CH:31]2

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 58012-AminophenolHCID 11412697Thiocarbonyl diimidazoleHCID 675202746-(6,7-Dimethoxyquinolin-4-yloxy)naphthalen-1-amine

Product 1

HCID 59813846HCID 59813846, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

Thiocarbonyl diimidazole (113 mg, 0.65 mmol) was added to a mixture of 6-(6,7-dimethoxyquinolin-4-yloxy)naphthalene-1-amine (150 mg, 0.43 mmol), in CH2Cl2 (5 mL) at ambient temperature. After stirring for 3 h, the mixture was concentrated and the derived isothiocyanate was dissolved in MeCN (2 mL). A solution of 2-aminophenol (50 mg, 0.45 mmol) in MeCN (2 mL) was added and the mixture was stirred for 48 h at which point EDC (125 mg, 0.65 mmol) was introduced. The reaction was heated at 80° C. for 2 h. After cooling to ambient temperature, the suspension was filtered and the resulting solid was washed well with MeOH to furnish the title as a tan solid. MS (ESI, pos. ion) m/z: 464.1 (M+1). Mass Calc'd for C28H21N3O4: 463.48.

Workup

  1. concentrationthe mixture was concentrated
  2. dissolutionthe derived isothiocyanate was dissolved in MeCN (2 mL)
  3. additionwas introduced
  4. temperatureAfter cooling to ambient temperature
  5. filtrationthe suspension was filtered
  6. washthe resulting solid was washed well with MeOH
  7. customto furnish the title as a tan solid

Sources & evidence

ORD record
ord-24da04a45f0a4365b7cb305ef60667a1
Source dataset
uspto-grants-2012_05
Patent number
US08178557B2

Reaction notes

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