Sodium Azide → HCID 86662231, compound

HRID 1627300Notes

Reaction equation

HRID 1627300 reaction equation
CS(O[CH2:6][CH2:7][O:8][C:9]1[CH:14]=[C:13]([F:15])[C:12]([CH2:16][S:17][C:18]2[N:19]([C:35]3[CH:40]=[CH:39][C:38]([F:41])=[CH:37][CH:36]=3)[C:20]([C:23]([C:26]3[CH:31]=[CH:30][C:29]([Cl:32])=[C:28]([O:33][CH3:34])[CH:27]=3)([CH3:25])[CH3:24])=[CH:21][N:22]=2)=[C:11]([F:42])[CH:10]=1)(=O)=O.[N-:43]=[N+:44]=[N-:45].[Na+]>CN(C=O)C>[N:43]([CH2:6][CH2:7][O:8][C:9]1[CH:10]=[C:11]([F:42])[C:12]([CH2:16][S:17][C:18]2[N:19]([C:35]3[CH:36]=[CH:37][C:38]([F:41])=[CH:39][CH:40]=3)[C:20]([C:23]([C:26]3[CH:31]=[CH:30][C:29]([Cl:32])=[C:28]([O:33][CH3:34])[CH:27]=3)([CH3:24])[CH3:25])=[CH:21][N:22]=2)=[C:13]([F:15])[CH:14]=1)=[N+:44]=[N-:45]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 866622302-(4-((5-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-ylthio)methyl)-3,5-difluorophenoxy)ethyl methanesulfonate

Product 1

HCID 86662231HCID 86662231, compoundYield 87.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(4-((5-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-ylthio)methyl)-3,5-difluorophenoxy)ethyl methanesulfonate (400 mg, 0.624 mmol) in DMF (6 mL) at 0° C. was added NaN3 (60 mg, 0.922 mmol). After stirring 1 h, the residue was partitioned in EtOAc (20 mL) and water (20 mL). The organic layer was washed with 1M HCl (10 mL) and water (10 mL) successively, dried over MgSO4, filtered and evaporated. The residue was purified by column chromatography (CH2Cl2/MeOH=20:1) to give 2-(4-(2-azidoethoxy)-2,6-difluorobenzylthio)-5-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazole (320 mg, 87% yield) as a white foam. 1H NMR (400 MHz, CDCl3) δ 7.22 (s, 1H), 7.16 (d, J=8.24 Hz, 1H), 6.77 (t, 2H), 6.55 (d, J=2.09 Hz, 1H), 6.51 (dd, J=8.25 Hz, 1H), 6.39-6.32 (m, 4H), 4.05 (m, 4H), 3.78 (s, 3H), 3.60 (t, 2H), 1.49 (s, 6H).

Workup

  1. customthe residue was partitioned in EtOAc (20 mL)
  2. washThe organic layer was washed with 1M HCl (10 mL) and water (10 mL) successively
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by column chromatography (CH2Cl2/MeOH=20:1)

Sources & evidence

ORD record
ord-df5384d63def468ab38ad296f86d5a9d
Source dataset
uspto-grants-2014_07
Patent number
US08785488B2

Reaction notes

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