4-Chloro-6,7-dimethoxyquinoline → n-[6-(6,7-Dimethoxy(4-quinolyloxy))(2-naphthyl)](phenylmethoxy)carboxamide

HRID 1925239Notes

Reaction equation

HRID 1925239 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][CH:3]=1.[OH:16][C:17]1[CH:18]=[C:19]2[C:24](=[CH:25][CH:26]=1)[CH:23]=[C:22]([NH:27][C:28]([O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:29])[CH:21]=[CH:20]2>CN(C1C=CN=CC=1)C.C1(C)C=CC=CC=1>[CH3:13][O:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][C:8]=1[O:14][CH3:15])[N:5]=[CH:4][CH:3]=[C:2]2[O:16][C:17]1[CH:18]=[C:19]2[C:24](=[CH:25][CH:26]=1)[CH:23]=[C:22]([NH:27][C:28]([O:30][CH2:31][C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)=[O:29])[CH:21]=[CH:20]2

Participants

5

Reactant 2

HCID 4596104-Chloro-6,7-dimethoxyquinolineHCID 67520229benzyl N-(6-hydroxynaphthalen-2-yl)carbamate

Product 1

HCID 59813732n-[6-(6,7-Dimethoxy(4-quinolyloxy))(2-naphthyl)](phenylmethoxy)carboxamide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1140TolueneSolvent

Procedure

4-Chloro-6,7-dimethoxyquinoline (prepared by the method described in WO 03/33472) (223 mg, 1.0 mmol), N-(6-hydroxy-(2-naphthyl))(benzyloxy)carboxamide (Step a, 293 mg, 1.0 mmol) and DMAP (122 mg, 1.0 mmol, Aldrich) in toluene (5 mL, Aldrich) were microwaved (Personal Chemistry, Emrys Optimizer) at 180° C. for 2 h. After cooling to RT, the white precipitate was collected and purified by silica gel column chromatography (80% EtOAc/hexane) to give title compound as a white solid. MS (ESI, pos. ion) m/z: 481.3 (M+1). Mass Calc'd for C29H24N2O5: 480.17.

Workup

  1. customwere microwaved (Personal Chemistry, Emrys Optimizer) at 180° C. for 2 h
  2. customthe white precipitate was collected
  3. custompurified by silica gel column chromatography (80% EtOAc/hexane)

Sources & evidence

ORD record
ord-51f4881cc81a4d91822618509e17d35e
Source dataset
uspto-grants-2012_05
Patent number
US08178557B2

Reaction notes

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