Triphenylphosphine → 1-methyl-4-{3-[(2-pyridin-3-ylethyl)pyridin-4-ylmethylamino]propoxy}-1H-quinolin-2-one trihydrochloride

HRID 1504177Notes

Reaction equation

HRID 1504177 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.[OH:32][C:33]1[C:42]2[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=2)[N:36]([CH3:43])[C:35](=[O:44])[CH:34]=1.[N:45]1[CH:50]=[CH:49][CH:48]=[C:47]([CH2:51][CH2:52][N:53]([CH2:58][C:59]2[CH:64]=[CH:63][N:62]=[CH:61][CH:60]=2)[CH2:54][CH2:55][CH2:56]O)[CH:46]=1.C(OC(=O)C)C.[ClH:71]>C(OCC)(=O)C.O1CCCC1>[ClH:71].[ClH:71].[ClH:71].[CH3:43][N:36]1[C:37]2[C:42](=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:33]([O:32][CH2:56][CH2:55][CH2:54][N:53]([CH2:52][CH2:51][C:47]2[CH:46]=[N:45][CH:50]=[CH:49][CH:48]=2)[CH2:58][C:59]2[CH:64]=[CH:63][N:62]=[CH:61][CH:60]=2)=[CH:34][C:35]1=[O:44]

Participants

8

Reactant 5

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 21866389Hydrogen chloride-ethyl acetateHCID 546864364-Hydroxy-N-methylcarbostyrilHCID 669609373-[(2-Pyridin-3-ylethyl)pyridin-4-ylmethylamino]propan-1-ol

Product 1

HCID 706566631-methyl-4-{3-[(2-pyridin-3-ylethyl)pyridin-4-ylmethylamino]propoxy}-1H-quinolin-2-one trihydrochloride

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Triphenyl phosphine(102 mg) and diethyl azodicarboxylate(68 mg) were added to a tetrahydrofuran (THF) solution(5 ml) of 4-hydroxy-1-methyl-1H-quinolin-2-one(63 mg), and 3-[(2-pyridin-3-ylethyl)pyridin-4-ylmethylamino]propane-1-ol(81.4 mg). The mixture was stirred overnight. After the reaction mixture was condensed under reduced pressure, the residue was purified by silica gel column chromatography (dichloromethane: methanol=20:1→10:1). The purified product was condensed under reduced pressure. A 4N-hydrogen chloride ethyl acetate solution(0.29 ml) was added to an ethyl acetate solution of the residue, which was stirred at room temperature for 30 minutes. The generated insoluble matter was separated by filtration, and dried to give the title compound(126.8 mg) as a white powder.

Workup

  1. customcondensed under reduced pressure
  2. customthe residue was purified by silica gel column chromatography (dichloromethane: methanol=20:1→10:1)
  3. customcondensed under reduced pressure
  4. stirringwas stirred at room temperature for 30 minutes
  5. customThe generated insoluble matter was separated by filtration
  6. customdried

Sources & evidence

ORD record
ord-1c62243170884866817dae8772968b71
Source dataset
uspto-grants-2015_12
Patent number
US09212187B2

Reaction notes

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