2-Aminoquinoline → HCID 66965562, compound

HRID 1514902Notes

Reaction equation

HRID 1514902 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([F:11])([F:10])[F:9])[C:3]=1[C:12]1[NH:13][C:14]2[CH:20]=[C:19]([C:21](Cl)=[O:22])[CH:18]=[CH:17][C:15]=2[N:16]=1.[N:24]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:27]=[CH:26][C:25]=1[NH2:34].CCN(C(C)C)C(C)C>C1COCC1>[N:24]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:27]=[CH:26][C:25]=1[NH:34][C:21]([C:19]1[CH:18]=[CH:17][C:15]2[N:16]=[C:12]([C:3]3[C:4]([C:8]([F:10])([F:11])[F:9])=[CH:5][CH:6]=[CH:7][C:2]=3[Cl:1])[NH:13][C:14]=2[CH:20]=1)=[O:22]

Participants

5

Reactant 3

HCID 113792-AminoquinolineHCID 81531DiisopropylethylamineHCID 86651262HCID 86651262, compound

Product 1

HCID 66965562HCID 66965562, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred suspension of 2-(2-chloro-6-trifluoromethylphenyl)-3H-benzoimidazole-5-carbonyl chloride (394 mg, 1.0 mmol) and quinolin-2-ylamine (144 mg, 1.0 mmol) in THF (6 mL) was added DIPEA (0.53 ml, 3.0 mmol). The solution was heated at 60° C. for 2 days and the reaction was quenched with water and aqueous layer was extracted with EtOAc. The organic layer was washed with water, brine, dried with MgSO4, and filtered. The solvent was removed under reduced pressure and the residue was purified by flash chromatography using heptane/EtOAc (1:4) as eluent to give 2-(2-chloro-6-trifluoromethylphenyl)-3H-benzoimidazole-5-carboxylic acid quinolin-2-ylamide as a white solid. 1H NMR (Methanol-d4, 400 MHz): δ 8.45 (d, 1H), 8.37 (d, 1H), 8.08 (d, 1H), 7.94 (m, 4H), 7.83 (m, 1H), 7.74 (m, 1H), 7.54 (m, 1H). MS (m/z) 467.1 (M+1); Retention time: 1.45 min (Method 10).

Workup

  1. customthe reaction was quenched with water and aqueous layer
  2. extractionwas extracted with EtOAc
  3. washThe organic layer was washed with water, brine
  4. dry with materialdried with MgSO4
  5. filtrationfiltered
  6. customThe solvent was removed under reduced pressure
  7. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-5d9b9cb3ae814e679b8eef17cab67ae7
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

Loading…