Potassium Hydroxide → N-{6-[6-Methoxy-7-(2-pyrrolidin-1-yl-ethoxy)-quinolin-4-yloxy]-naphthalen-1-yl}-benzamide

HRID 1925276Notes

Reaction equation

HRID 1925276 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([NH:12][C:13](=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[CH:7][CH:6]=[CH:5]2.Cl[C:22]1[C:31]2[C:26](=[CH:27][C:28]([O:34][CH2:35][CH2:36][N:37]3[CH2:41][CH2:40][CH2:39][CH2:38]3)=[C:29]([O:32][CH3:33])[CH:30]=2)[N:25]=[CH:24][CH:23]=1.[OH-].[K+]>CN(C=O)C.N1C=CC=CC=1.C(Cl)Cl.O.[Cu]>[CH3:33][O:32][C:29]1[CH:30]=[C:31]2[C:26](=[CH:27][C:28]=1[O:34][CH2:35][CH2:36][N:37]1[CH2:41][CH2:40][CH2:39][CH2:38]1)[N:25]=[CH:24][CH:23]=[C:22]2[O:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([NH:12][C:13](=[O:20])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)=[CH:7][CH:6]=[CH:5]2

Participants

9

Reactant 3

HCID 14797Potassium HydroxideHCID 675201424-Chloro-6-methoxy-7-(2-pyrrolidin-1-yl-ethoxy)-quinolineHCID 67520279N-(6-Hydroxy-naphthalen-1-yl)-benzamide

Product 1

HCID 59813344N-{6-[6-Methoxy-7-(2-pyrrolidin-1-yl-ethoxy)-quinolin-4-yloxy]-naphthalen-1-yl}-benzamide

Reagents, catalysts & solvents 5

HCID 23978CopperCatalystHCID 962WaterSolventHCID 1049PyridineSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
120 °C

Procedure

To a microwaveable vial containing 0.300 g (0.0011 mmol) of N-(6-hydroxy-naphthalen-1-yl)-benzamide in 1.5 mL DMF and 1.5 mL pyridine, was added 0.858 g (0.0028 mmol) of 4-chloro-6-methoxy-7-(2-pyrrolidin-1-yl-ethoxy)-quinoline. Copper grind was added (5 mmol %) to the mixture, along with 0.158 g (0.0025 mmol) KOH pellets. The vial was heated in a microwave for 18 min at 120° C., (60 Watts of constant power, powermax, CEM). The mixture was diluted with CH2Cl2 and water, then transferred to a seperatory funnel. The organics were extracted 3× with CH2Cl2. Then combined all organics, dried over Na2SO4, filtered, and concentrated in-vacuo. The crude was purified by reverse-phase HPLC. A tan oil was collected, which was the titled product. MS (ESI pos. ion) m/z: 534 (M+H). Calc'd for C33H31N3O4−533.23.

Workup

  1. additionwas added (5 mmol %) to the mixture
  2. customtransferred to a seperatory funnel
  3. extractionThe organics were extracted 3× with CH2Cl2
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in-vacuo
  7. customThe crude was purified by reverse-phase HPLC
  8. customA tan oil was collected

Sources & evidence

ORD record
ord-ac3fb048c0ac4a1f90af39b4960a7456
Source dataset
uspto-grants-2012_05
Patent number
US08178557B2

Reaction notes

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