Water → HCID 89435362, compound

HRID 1774675Notes

Reaction equation

HRID 1774675 reaction equation
C1(O[C:8](=[O:42])[O:9][CH2:10][N:11]2[C:20]3[C:15](=[CH:16][CH:17]=[C:18]([O:21][CH2:22][CH2:23][CH2:24][CH2:25][N:26]4[CH2:31][CH2:30][N:29]([C:32]5[C:40]6[CH:39]=[CH:38][S:37][C:36]=6[CH:35]=[CH:34][CH:33]=5)[CH2:28][CH2:27]4)[CH:19]=3)[CH2:14][CH2:13][C:12]2=[O:41])C=CC=CC=1.[NH:43]1[CH2:48][CH2:47][CH2:46][CH2:45][CH2:44]1.N12CCCN=C1CCCCC2.O>C1COCC1>[S:37]1[CH:38]=[CH:39][C:40]2[C:32]([N:29]3[CH2:28][CH2:27][N:26]([CH2:25][CH2:24][CH2:23][CH2:22][O:21][C:18]4[CH:19]=[C:20]5[C:15]([CH2:14][CH2:13][C:12](=[O:41])[N:11]5[CH2:10][O:9][C:8]([N:43]5[CH2:48][CH2:47][CH2:46][CH2:45][CH2:44]5)=[O:42])=[CH:16][CH:17]=4)[CH2:31][CH2:30]3)=[CH:33][CH:34]=[CH:35][C:36]1=2

Participants

6

Reactant 4

HCID 962WaterHCID 8082PiperidineHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 86273004HCID 86273004, compound

Product 1

HCID 89435362HCID 89435362, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution (3 ml) of carbonic acid 7-[4-(4-benzo[b]thiophen-4-ylpiperazin-1-yl)butoxy]-2-oxo-3,4-dihydro-2H-quinolin-1-ylmethyl ester phenyl ester (0.29 g) synthesized in the same manner as in Example 5 in THF were added piperidine (0.5 ml) and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) (0.05 ml), and the mixture was stirred at room temperature for 16 hr. Water was added and the reaction mixture was extracted with ethyl acetate, dried over sodium sulfate, and concentrated under reduced pressure. The residue was purified by moderate-pressure basic silica gel column chromatography (hexane:ethyl acetate=1:0 to 1:1) to remove phenol, and concentrated under reduced pressure. The residue was purified by moderate-pressure silica gel column chromatography (hexane:ethyl acetate=1:0 to 0:1) to give the title compound (yield 0.21 g, 74%) as a colorless oil.

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by moderate-pressure basic silica gel column chromatography (hexane:ethyl acetate=1:0 to 1:1)
  5. customto remove phenol
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by moderate-pressure silica gel column chromatography (hexane:ethyl acetate=1:0 to 0:1)

Sources & evidence

ORD record
ord-6cfa53b34b55415ea195886084d198e2
Source dataset
uspto-grants-2016_02
Patent number
US09260420B2

Reaction notes

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