Morpholine → HCID 178511933, compound

HRID 1928843Notes

Reaction equation

HRID 1928843 reaction equation
I.[C@H:2]1([NH:11][C:12]2[CH:21]=[CH:20][C:19]3[C:14](=[CH:15][CH:16]=[C:17]([NH:22][C:23](=[NH:26])SC)[CH:18]=3)[N:13]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3]1.[NH:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1>C(O)C>[C@H:2]1([NH:11][C:12]2[CH:21]=[CH:20][C:19]3[C:14](=[CH:15][CH:16]=[C:17]([NH:22][C:23]([N:27]4[CH2:32][CH2:31][O:30][CH2:29][CH2:28]4)=[NH:26])[CH:18]=3)[N:13]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 178503968HCID 178503968, compound

Product 1

HCID 178511933HCID 178511933, compoundYield 51.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-[2-((R)-Indan-1-ylamino)-quinolin-6-yl]-2-methyl-isothiourea hydroiodide (345 mg, 0.72 mmol) was dissolved in 10 mL ethanol. Morpholine (350 mg, 4 mmol) was added and the reaction mixture was refluxed overnight. The solvent was evaporated and the residue was purified by column chromatography (silica gel, dichloromethane/methanol 40:1). The title compound (144 mg, 51%) was obtained as a light yellow foam; MS: m/e=388.3 (M+H+).

Workup

  1. temperaturethe reaction mixture was refluxed overnight
  2. customThe solvent was evaporated
  3. customthe residue was purified by column chromatography (silica gel, dichloromethane/methanol 40:1)

Sources & evidence

ORD record
ord-dbb56f1a20b2416c9e0894c3587ead48
Source dataset
uspto-grants-2012_05
Patent number
US08183380B2

Reaction notes

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