Ammonia → HCID 66885284, compound

HRID 1916244Notes

Reaction equation

HRID 1916244 reaction equation
C([N:3](CC)CC)C.ClC(OCC(C)C)=O.[S:16]1[CH:20]=[CH:19][C:18]2[C:21]([N:25]3[CH2:30][CH2:29][N:28]([CH2:31][CH2:32][CH2:33][O:34][C:35]4[C:44]5[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=5)[N:38]=[C:37]([C:45](O)=[O:46])[CH:36]=4)[CH2:27][CH2:26]3)=[CH:22][CH:23]=[CH:24][C:17]1=2.N>C(#N)C.C(OCC)(=O)C>[S:16]1[CH:20]=[CH:19][C:18]2[C:21]([N:25]3[CH2:30][CH2:29][N:28]([CH2:31][CH2:32][CH2:33][O:34][C:35]4[C:44]5[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=5)[N:38]=[C:37]([C:45]([NH2:3])=[O:46])[CH:36]=4)[CH2:27][CH2:26]3)=[CH:22][CH:23]=[CH:24][C:17]1=2

Participants

7

Reactant 4

HCID 222AmmoniaHCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 66885320HCID 66885320, compound

Product 1

HCID 66885284HCID 66885284, compoundYield 16%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Triethylamine (0.25 ml, 1.8 mmol) and isobutyl chloroformate (0.19 ml, 1.4 mmol) were added to a solution (10 ml) of 4-[3-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)propoxy]quinolin-2-carboxylic acid (0.53 g, 1.2 mmol) in acetonitrile with cooling in an ice-bath, followed by stirring at 0° C. for 3 hours. 28% Aqueous ammonia (0.15 ml) was added thereto and the reaction mixture was stirred at room temperature for 5 minutes. Ethyl acetate was further added thereto, then the reaction mixture was washed with water and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (n-hexane:ethyl acetate=3:1), and concentrated under reduced pressure. The residue (0.2 g) was dissolved and recrystallized from the mixed solvent of ethyl acetate and isopropyl ether to obtain 4-[3-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)propoxy]-quinolin-2-carboxamide (79 mg, yield: 16%) as white powder.

Workup

  1. temperaturewith cooling in an ice-bath
  2. stirringthe reaction mixture was stirred at room temperature for 5 minutes
  3. washthe reaction mixture was washed with water
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by basic silica gel column chromatography (n-hexane:ethyl acetate=3:1)
  6. concentrationconcentrated under reduced pressure
  7. dissolutionThe residue (0.2 g) was dissolved
  8. customrecrystallized from the mixed solvent of ethyl acetate and isopropyl ether

Sources & evidence

ORD record
ord-186f752c39734489a7542efd3797eaab
Source dataset
uspto-grants-2013_12
Patent number
US08618109B2

Reaction notes

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