Lansoprazole → HCID 59769506, compound

HRID 2096065Notes

Reaction equation

HRID 2096065 reaction equation
[C:1]([O:4][CH2:5][CH2:6][N:7]([C:14](Cl)=[O:15])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)(=[O:3])[CH3:2].[CH3:17][C:18]1[C:19]([CH2:30][S:31]([C:33]2[NH:37][C:36]3[CH:38]=[CH:39][CH:40]=[CH:41][C:35]=3[N:34]=2)=[O:32])=[N:20][CH:21]=[CH:22][C:23]=1[O:24][CH2:25][C:26]([F:29])([F:28])[F:27].C(N(CC)CC)C.C(OCC)(=O)C>O1CCCC1.CN(C)C1C=CN=CC=1>[C:1]([O:4][CH2:5][CH2:6][N:7]([C:14]([N:34]1[C:35]2[CH:41]=[CH:40][CH:39]=[CH:38][C:36]=2[N:37]=[C:33]1[S:31]([CH2:30][C:19]1[C:18]([CH3:17])=[C:23]([O:24][CH2:25][C:26]([F:27])([F:28])[F:29])[CH:22]=[CH:21][N:20]=1)=[O:32])=[O:15])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 3883LansoprazoleHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 85900220HCID 85900220, compound

Product 1

HCID 59769506HCID 59769506, compoundYield 68.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2-[(chlorocarbonyl)(phenyl)amino]ethyl acetate (0.58 g) prepared in the same way as in Synthetic Example 25 in tetrahydrofuran (10 mL) were added 2-[[[3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridyl]methyl]sulfinyl]-1H-benzimidazole (0.73 g), triethylamine (0.558 mL) and 4-dimethylaminopyridine (0.024 g), and stirred at 60° C. for 15 hrs. To the reaction solution was added ethyl acetate (30 mL), and washed with water (50 mL) and saturated brine (50 mL), and then, dried over anhydrous sodium sulfate, followed by concentrating under reduced pressure. The residue was purified with flash silica gel column chromatography (eluted with acetone:hexane=1:4, then 3:2). The purified material was crystallized from diethyl ether to give title compound as white solid (0.779 g).

Workup

  1. washwashed with water (50 mL) and saturated brine (50 mL)
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationby concentrating under reduced pressure
  4. customThe residue was purified with flash silica gel column chromatography (
  5. washeluted with acetone
  6. customThe purified material was crystallized from diethyl ether

Sources & evidence

ORD record
ord-5c19b1df14824592a08a8cb04795ad9f
Source dataset
uspto-grants-2013_05
Patent number
US08449911B2

Reaction notes

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