2-Chlorobenzoxazole → N-(Benzoxazol-2-yl)-N-3-(4-methoxyphenoxy)propyl-3-tert-butyldimethylsilyloxybenzylamine

HRID 350841Notes

Reaction equation

HRID 350841 reaction equation
[CH3:1][O:2][C:3]1[CH:28]=[CH:27][C:6]([O:7][CH2:8][CH2:9][CH2:10][NH:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])[CH:14]=2)=[CH:5][CH:4]=1.C(N(CC)C(C)C)(C)C.Cl[C:39]1[O:40][C:41]2[CH:47]=[CH:46][CH:45]=[CH:44][C:42]=2[N:43]=1>CN(C)C=O>[O:40]1[C:41]2[CH:47]=[CH:46][CH:45]=[CH:44][C:42]=2[N:43]=[C:39]1[N:11]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][Si:20]([C:23]([CH3:24])([CH3:25])[CH3:26])([CH3:21])[CH3:22])[CH:14]=1)[CH2:10][CH2:9][CH2:8][O:7][C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 119862-ChlorobenzoxazoleHCID 81531DiisopropylethylamineHCID 21949684n-3-(4-Methoxyphenoxy)propyl-3-tert-butyldimethylsilyloxybenzylamine

Product 1

HCID 21949679N-(Benzoxazol-2-yl)-N-3-(4-methoxyphenoxy)propyl-3-tert-butyldimethylsilyloxybenzylamine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-3-(4-methoxyphenoxy)propyl-3-tert-butyldimethylsilyloxybenzylamine (1.9 g, 5.0 mmol) was dissolved in N,N-dimethylformamide (3.0 mL). Subsequently, N,N-diisopropylethylamine (768 mg, 5.9 mmol) was added dropwise thereto. To the solution, 2-chlorobenzoxazole (912 mg, 5.94 mmol) was added. The mixture was stirred for 15 minutes at room temperature, and then stirred overnight at 70° C. The resultant mixture was extracted with ethyl acetate, followed by washing the organic layer with brine, drying over anhydrous sodium sulfate, and concentration under reduced pressure. The resultant mixture was subjected to purification by silica gel column chromatography (n-hexane/ethyl acetate=10/1), whereby the target compound was obtained (1.9 g, 73%).

Workup

  1. stirringstirred overnight at 70° C
  2. extractionThe resultant mixture was extracted with ethyl acetate
  3. washby washing the organic layer with brine
  4. dry with materialdrying over anhydrous sodium sulfate, and concentration under reduced pressure
  5. customThe resultant mixture was subjected to purification by silica gel column chromatography (n-hexane/ethyl acetate=10/1), whereby the target compound
  6. customwas obtained (1.9 g, 73%)

Sources & evidence

ORD record
ord-8d6d3f2bb52a44e7984c0df1e897ddff
Source dataset
uspto-grants-2007_02
Patent number
US07183295B2

Reaction notes

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