Water → HCID 117856251, compound

HRID 1774689Notes

Reaction equation

HRID 1774689 reaction equation
C(O)CCCCC.[H-].[Na+].[C:10]1([O:16][C:17](=[O:51])[O:18][CH2:19][N:20]2[C:29]3[C:24](=[CH:25][CH:26]=[C:27]([O:30][CH2:31][CH2:32][CH2:33][CH2:34][N:35]4[CH2:40][CH2:39][N:38]([C:41]5[C:49]6[CH:48]=[CH:47][S:46][C:45]=6[CH:44]=[CH:43][CH:42]=5)[CH2:37][CH2:36]4)[CH:28]=3)[CH:23]=[CH:22][C:21]2=[O:50])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.O>O1CCCC1>[CH2:10]([O:16][C:17](=[O:51])[O:18][CH2:19][N:20]1[C:29]2[C:24](=[CH:25][CH:26]=[C:27]([O:30][CH2:31][CH2:32][CH2:33][CH2:34][N:35]3[CH2:40][CH2:39][N:38]([C:41]4[C:49]5[CH:48]=[CH:47][S:46][C:45]=5[CH:44]=[CH:43][CH:42]=4)[CH2:37][CH2:36]3)[CH:28]=2)[CH:23]=[CH:22][C:21]1=[O:50])[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15]

Participants

6

Reactant 4

HCID 962WaterHCID 81031-HexanolHCID 24758Sodium hydrideHCID 89435206HCID 89435206, compound

Product 1

HCID 117856251HCID 117856251, compoundYield 12.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of n-hexylalcohol (50.5 mg) in tetrahydrofuran (5 ml) was added with stirring under ice-cooling 60% sodium hydride (18 mg) by small portions, and the mixture was stirred at the same temperature for 0.5 hr, a solution of carbonic acid 7-[4-(4-benzo[b]thiophen-4-ylpiperazin-1-yl)butoxy]-2-oxo-2H-quinolin-1-ylmethyl ester phenyl ester (240 mg) in tetrahydrofuran (1 ml) was added dropwise, and the mixture was stirred under ice-cooling for 3 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate, and dried over sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate) to give carbonic acid 7-[4-(4-benzo[b]thiophen-4-ylpiperazin-1-yl)butoxy]-2-oxo-2H-quinolin-1-ylmethyl ester hexyl ester (30 mg).

Workup

  1. stirringthe mixture was stirred at the same temperature for 0.5 hr
  2. stirringthe mixture was stirred under ice-
  3. temperaturecooling for 3 hr
  4. extractionthe mixture was extracted with ethyl acetate
  5. dry with materialdried over sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-fdee6a2baf854e648cd84122d345e7ea
Source dataset
uspto-grants-2016_02
Patent number
US09260420B2

Reaction notes

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