Water → HCID 117855853, compound

HRID 1774685Notes

Reaction equation

HRID 1774685 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]([CH:25]=[CH:26][C:27](=[O:31])[NH:28]5)=[CH:23][CH:22]=4)[CH2:12][CH2:11]3)=[CH:7][CH:8]=[CH:9][C:2]1=2.[H-].[Na+].[C:34](=[O:48])([O-:47])[O:35][C:36]1[CH:41]=[CH:40][C:39]([N+:42]([O-:44])=[O:43])=[CH:38][C:37]=1CCl.O.[CH2:50]1COCC1>>[N+:42]([C:39]1[CH:40]=[CH:41][C:36]([O:35][C:34](=[O:48])[O:47][CH2:50][N:28]2[C:29]3[C:24](=[CH:23][CH:22]=[C:21]([O:20][CH2:19][CH2:18][CH2:17][CH2:16][N:13]4[CH2:12][CH2:11][N:10]([C:6]5[C:3]6[CH:4]=[CH:5][S:1][C:2]=6[CH:9]=[CH:8][CH:7]=5)[CH2:15][CH2:14]4)[CH:30]=3)[CH:25]=[CH:26][C:27]2=[O:31])=[CH:37][CH:38]=1)([O-:44])=[O:43]

Participants

6

Reactant 5

HCID 962WaterHCID 8028Tetrahydrofuran2×HCID 24758Sodium hydrideHCID 11978813BrexpiprazoleHCID 68469603HCID 68469603, compound

Product 1

HCID 117855853HCID 117855853, compound

Conditions

Temperature
-70 °C

Procedure

7-[4-(4-Benzo[b]thiophen-4-ylpiperazin-1-yl)butoxy]-1H-quinolin-2-one (2.0 g) was suspended in anhydrous THF (40 ml) under a nitrogen atmosphere, and sodium hydride (about 55% oil) (0.22 g) was added. The mixture was refluxed for 30 min under a nitrogen atmosphere. The obtained solution was cooled to was cooled to −70° C., and a solution (20 ml) of chloromethyl-4-nitrophenyl carbonate (1.50 g) in anhydrous THF with cannula. The reaction mixture was stirred at room temperature for 3 hr. Water was added to the reaction mixture to discontinue the reaction, and the mixture was extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and concentrated by filtration. The obtained residue was purified by silica gel column chromatography (ethyl acetate) to give the component (Rf value: 0.62, ethyl acetate, 0.67 g) as a pale-yellow amorphous compound. The obtained compound was used for the next reaction step without further purification.

Workup

  1. temperatureThe mixture was refluxed for 30 min under a nitrogen atmosphere
  2. temperatureThe obtained solution was cooled
  3. customthe reaction
  4. extractionthe mixture was extracted with ethyl acetate
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. concentrationconcentrated by filtration
  7. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate)
  8. customto give the component (Rf value: 0.62, ethyl acetate, 0.67 g) as a pale-yellow amorphous compound
  9. customThe obtained compound was used for the next reaction step without further purification

Sources & evidence

ORD record
ord-3b9eb42461404f6da460bceb9a5144f7
Source dataset
uspto-grants-2016_02
Patent number
US09260420B2

Reaction notes

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