Cilostazol → HCID 58443368, compound

HRID 1969368Notes

Reaction equation

HRID 1969368 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.C(N(CC)CC)C.[Br:35][CH2:36][CH:37]([CH2:42][Br:43])[CH2:38][C:39](Cl)=[O:40]>C1COCC1>[Br:35][CH2:36][CH:37]([CH2:42][Br:43])[CH2:38][C:39]([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:40]

Participants

5

Reactant 3

HCID 2754Cilostazol2×HCID 8471TriethylamineHCID 86657759HCID 86657759, compound

Product 1

HCID 58443368HCID 58443368, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 6-[4-(1-cyclohexyl-1H-tetrazol-5-yl)butoxy]-3,4-dihydroquinolin-2(1H)-one (cilostazol, 1, A=H, 2.0 g, 3.50 mmol), N,N-dimethylaminopyridine (0.043 g, 0.35 mmol) and triethylamine (0.5 ml, 0.35 mmol) in THF (100 mL) at 0° C. and under nitrogen, a solution of 4-bromo-3-(bromomethyl)butanoyl chloride (0.97 g, 3.50 mmol) in THF (5 mL) is slowly added and the reaction mixture stirred at room temperature for 2 hours. Then it is partitioned between ethyl acetate and phosphate buffer (pH=3) and extracted with ethyl acetate (3×25 mL). The organic phase is dried over Na2SO4 and concentrated. The crude material is purified by flash chromatography (CH2Cl2/acetone 7:3).

Workup

  1. customThen it is partitioned between ethyl acetate and phosphate buffer (pH=3)
  2. extractionextracted with ethyl acetate (3×25 mL)
  3. dry with materialThe organic phase is dried over Na2SO4
  4. concentrationconcentrated
  5. customThe crude material is purified by flash chromatography (CH2Cl2/acetone 7:3)

Sources & evidence

ORD record
ord-f6084c3fbc9b447f8535f71e425ebc04
Source dataset
uspto-grants-2013_04
Patent number
US08426597B2

Reaction notes

Loading…