Sodium Chloride → 1-(2-(2-((5-ethoxy-2-fluoro-3-isopropoxyphenyl)(4-(5-methyl-1,2,4-oxadiazol-3-yl)phenylamino)methyl)-1-trityl-1H-imidazol-4-yl)phenyl)propan-1-ol

HRID 2104984Notes

Reaction equation

HRID 2104984 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([O:57][CH:58]([CH3:60])[CH3:59])[C:7]([F:56])=[C:8]([CH:10]([NH:43][C:44]2[CH:49]=[CH:48][C:47]([C:50]3[N:54]=[C:53]([CH3:55])[O:52][N:51]=3)=[CH:46][CH:45]=2)[C:11]2[N:12]([C:24]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH:13]=[C:14]([C:16]3[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=3[CH:18]=[O:19])[N:15]=2)[CH:9]=1)[CH3:2].[CH3:61][CH2:62][Mg+].[Br-].CCOC(C)=O.[Na+].[Cl-]>C1COCC1>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([O:57][CH:58]([CH3:59])[CH3:60])[C:7]([F:56])=[C:8]([CH:10]([NH:43][C:44]2[CH:45]=[CH:46][C:47]([C:50]3[N:54]=[C:53]([CH3:55])[O:52][N:51]=3)=[CH:48][CH:49]=2)[C:11]2[N:12]([C:24]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH:13]=[C:14]([C:16]3[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=3[CH:18]([OH:19])[CH2:61][CH3:62])[N:15]=2)[CH:9]=1)[CH3:2]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 8857Ethyl AcetateHCID 866079362-(2-((5-ethoxy-2-fluoro-3-isopropoxyphenyl)(4-(5-methyl-1,2,4-oxadiazol-3-yl)phenylamino)methyl)-1-trityl-1H-imidazol-4-yl)benzaldehydeHCID 178461630HCID 178461630, compound

Product 1

HCID 688125741-(2-(2-((5-ethoxy-2-fluoro-3-isopropoxyphenyl)(4-(5-methyl-1,2,4-oxadiazol-3-yl)phenylamino)methyl)-1-trityl-1H-imidazol-4-yl)phenyl)propan-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of Intermediate 122.1 (50 mg, 0.06 mmol) in THF (1 mL) was added EtMgBr dropwise at 0° C. under N2 atmosphere, the reaction mixture was stirred at 0° C. for 30 min. The reaction mixture was then partionated between EtOAc and sat. NaCl, the organic layer was collected and dried over (Na2SO4), filtered and concentrated. The crude material Intermediate 122.2 was used as is in the following step. LCMS (2 min gradient) RT=2.23 min, 828.4 (M+H).

Workup

  1. customthe organic layer was collected
  2. dry with materialdried over (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customLCMS (2 min gradient) RT=2.23 min, 828.4 (M+H)

Sources & evidence

ORD record
ord-02e3a39cfd894ebeae8266a847b3b507
Source dataset
uspto-grants-2009_08
Patent number
US07576098B2

Reaction notes

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