Pyridine → HCID 89435367, compound

HRID 1774687Notes

Reaction equation

HRID 1774687 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]2[C:6]([N:10]3[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH2:18][CH2:19][O:20][C:21]4[CH:30]=[C:29]5[C:24]([C:25]([CH3:35])([CH3:34])[CH2:26][C:27](=[O:33])[N:28]5[CH2:31][OH:32])=[CH:23][CH:22]=4)[CH2:12][CH2:11]3)=[CH:7][CH:8]=[CH:9][C:2]1=2.S1C=CC2C(N3CCN(CCCCOC4C=C5C(C(C)(C)CC(=O)N5)=CC=4)CC3)=CC=CC1=2.N1C=CC=CC=1.Cl[C:76]([O:78][CH2:79][CH2:80][CH2:81][CH2:82][CH2:83][CH2:84][CH2:85][CH2:86][CH2:87][CH3:88])=[O:77]>C(Cl)Cl.O>[CH2:79]([O:78][C:76](=[O:77])[O:32][CH2:31][N:28]1[C:29]2[C:24](=[CH:23][CH:22]=[C:21]([O:20][CH2:19][CH2:18][CH2:17][CH2:16][N:13]3[CH2:14][CH2:15][N:10]([C:6]4[C:3]5[CH:4]=[CH:5][S:1][C:2]=5[CH:9]=[CH:8][CH:7]=4)[CH2:11][CH2:12]3)[CH:30]=2)[C:25]([CH3:35])([CH3:34])[CH2:26][C:27]1=[O:33])[CH2:80][CH2:81][CH2:82][CH2:83][CH2:84][CH2:85][CH2:86][CH2:87][CH3:88]

Participants

7

Reactant 4

HCID 1049PyridineHCID 108727Decyl chloroformateHCID 71295512HCID 71295512, compoundHCID 89435480HCID 89435480, compound

Product 1

HCID 89435367HCID 89435367, compoundYield 34.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

7-[4-(4-Benzo[b]thiophen-4-ylpiperazin-1-yl)butoxy]-1-hydroxymethyl-4,4-dimethyl-3,4-dihydro-1H-quinolin-2-one (460 mg), which is a mixture with 7-[4-(4-benzo[b]thiophen-4-ylpiperazin-1-yl)butoxy]-4,4-dimethyl-3,4-dihydro-1H-quinolin-2-one obtained in Example 155, was suspended in methylene chloride (10 ml), pyridine (0.06 ml) and decyl chloroformate (103 mg) were added, and the mixture was stirred under ice-cooling for 4 hr. Water was added to the reaction mixture, and the mixture was extracted with methylene chloride, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=2:1) to give carbonic acid 7-[4-(4-benzo[b]thiophen-4-ylpiperazin-1-yl)-butoxy]-4,4-dimethyl-2-oxo-3,4-dihydro-2H-quinolin-1-ylmethyl ester decyl ester (108 mg).

Workup

  1. temperaturecooling for 4 hr
  2. extractionthe mixture was extracted with methylene chloride
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=2:1)

Sources & evidence

ORD record
ord-23ed88a71f304911afe5475fe4f8629d
Source dataset
uspto-grants-2016_02
Patent number
US09260420B2

Reaction notes

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