8-Aminoquinoline → HCID 178506091, compound

HRID 33548

Reaction equation

HRID 33548 reaction equation
Cl[C:2]1[NH:6][C:5]2[CH:7]=[CH:8][C:9]([C:11]([F:14])([F:13])[F:12])=[CH:10][C:4]=2[N:3]=1.[NH2:15][C:16]1[CH:17]=[CH:18][CH:19]=[C:20]2[C:25]=1[N:24]=[CH:23][CH:22]=[CH:21]2>CCO>[F:12][C:11]([F:14])([F:13])[C:9]1[CH:8]=[CH:7][C:5]2[NH:6][C:2]([NH:15][C:16]3[CH:17]=[CH:18][CH:19]=[C:20]4[C:25]=3[N:24]=[CH:23][CH:22]=[CH:21]4)=[N:3][C:4]=2[CH:10]=1

Participants

4

Reactant 2

HCID 113598-AminoquinolineHCID 178506089HCID 178506089, compound

Product 1

HCID 178506091HCID 178506091, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-chloro-5-(trifluoromethyl)-1H-benzo[d]imidazole (66 mg, 0.3 mol, prepared according to the procedure described in WO 2004/035549 A1) and 8-aminoquinoline (29 mg, 0.6 mmol, Aldrich) in EtOH (2 mL) was subjected to microwave irradiation at 170° C. with stirring for 30 min. The reaction mixture was allowed to cool to room temperature, the solvent was removed in vacuo and the residue was purified by silica gel chromatography eluting with 3% MeOH/DCM to give the title compound as an amorphous solid. MS (ESI, pos. ion) m/z: 329 (M+1).

Workup

  1. customprepared
  2. customirradiation at 170° C.
  3. customthe solvent was removed in vacuo
  4. customthe residue was purified by silica gel chromatography
  5. washeluting with 3% MeOH/DCM

Sources & evidence

ORD record
ord-4383ea8f71fc4c7c8aa1855bfedd5fd1
Source dataset
uspto-grants-2008_09
Patent number
US07429608B2

Linked notes

Loading…