Water → 4-(2,3-Dihydro-1-benzofuran-4-ylamino)-8-methyl-7-(methylthio)-3-quinolinecarboxamide

HRID 230868Notes

Reaction equation

HRID 230868 reaction equation
Cl.Cl[C:3]1[C:12]([CH3:13])=[C:11]2[C:6]([C:7]([NH:17][C:18]3[C:23]4[CH2:24][CH2:25][O:26][C:22]=4[CH:21]=[CH:20][CH:19]=3)=[C:8]([C:14]([NH2:16])=[O:15])[CH:9]=[N:10]2)=[CH:5][CH:4]=1.[CH3:27][S-:28].[Na+].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O.[Cu]I>[O:26]1[C:22]2[CH:21]=[CH:20][CH:19]=[C:18]([NH:17][C:7]3[C:6]4[C:11](=[C:12]([CH3:13])[C:3]([S:28][CH3:27])=[CH:4][CH:5]=4)[N:10]=[CH:9][C:8]=3[C:14]([NH2:16])=[O:15])[C:23]=2[CH2:24][CH2:25]1

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 4378561Sodium methanethiolateHCID 674232657-Chloro-4-(2,3-dihydro-1-benzofuran-4-ylamino)-8-methyl-3-quinolinecarboxamide hydrochloride

Product 1

HCID 577632464-(2,3-Dihydro-1-benzofuran-4-ylamino)-8-methyl-7-(methylthio)-3-quinolinecarboxamideYield 34.8%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Procedure

A stirred mixture of Intermediate 104 (0.50 g), sodium methanethiolate (0.35 g), potassium carbonate (0.43 g) and copper (I) iodide (0.025 g) in dry N,N-dimethylformamide (3 ml) was heated at 100° under nitrogen for 18 h. The mixture was cooled, poured into water (50 ml) and stirred for 15 min. The solid material was filtered off, dried in vacuo at 80° for 2 h, and boiled in ethanol:water 15:1 (50 ml) for 30 min. The insoluble material was filtered off, and the filtrate evaporated to dryness to give the title compound as a pale yellow solid (0.163 g).

Workup

  1. temperaturewas heated at 100° under nitrogen for 18 h
  2. temperatureThe mixture was cooled
  3. filtrationThe solid material was filtered off
  4. customdried in vacuo at 80° for 2 h
  5. waitboiled in ethanol:water 15:1 (50 ml) for 30 min
  6. filtrationThe insoluble material was filtered off
  7. customthe filtrate evaporated to dryness

Sources & evidence

ORD record
ord-17c71c73c43b4ed39f54c63c4a589739
Source dataset
uspto-grants-2009_07
Patent number
US07566786B2

Reaction notes

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