Pyridine → HCID 58443370, compound

HRID 1969369Notes

Reaction equation

[CH:1]1([N:7]2[C:11]([CH2:12][CH2:13][CH2:14][CH2:15][O:16][C:17]3[CH:18]=[C:19]4[C:24](=[CH:25][CH:26]=3)[NH:23][C:22](=[O:27])[CH2:21][CH2:20]4)=[N:10][N:9]=[N:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.N1C=CC=CC=1.[Cl:34][CH2:35][CH2:36][CH2:37][C:38](Cl)=[O:39]>C(Cl)(Cl)Cl.C(Cl)Cl>[Cl:34][CH2:35][CH2:36][CH2:37][C:38]([N:23]1[C:24]2[C:19](=[CH:18][C:17]([O:16][CH2:15][CH2:14][CH2:13][CH2:12][C:11]3[N:7]([CH:1]4[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]4)[N:8]=[N:9][N:10]=3)=[CH:26][CH:25]=2)[CH2:20][CH2:21][C:22]1=[O:27])=[O:39]

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of 6-[4-(1-cyclohexyl-1H-tetrazol-5-yl)butoxy]-3,4-dihydroquinolin-2(1H)-one (cilostazol, 1, A=H, 15.00 g, 40.6 mmol), pyridine (6.42 g, 81.2 mmol) and 4-dimethyl-aminopyridine (DMAP, 6.45 g, 52.8 mmol) in 135 mL chloroform at room temperature is added slowly 4-chlorobutanoyl chloride (7.45 g, 52.8 mmol). The mixture is stirred at 70° C. for 20 hours. The reaction mixture is diluted with 1000 mL CH2Cl2, and washed with 1N HCl, saturated NaHCO3 solution and brine. The organic phase is dried over sodium sulphate, and concentrated. The residue is purified by flash chromatography (silica gel, CH2Cl2/tert-butyl methyl ether 90:10) to give the title compound in 42% yield.

Workup

washwashed with 1N HCl, saturated NaHCO3 solution and brine
dry with materialThe organic phase is dried over sodium sulphate
concentrationconcentrated
customThe residue is purified by flash chromatography (silica gel, CH2Cl2/tert-butyl methyl ether 90:10)

Sources & evidence

ORD record: ord-8d37c1dfceaf47b99324704f38ef32b8
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08426597B2

Reaction notes

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