Sodium Azide → HCID 86662233, compound

HRID 1627303Notes

Reaction equation

HRID 1627303 reaction equation
CS(O[CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[C:14]([F:16])[C:13]([CH2:17][S:18][C:19]2[N:20]([C:36]3[CH:41]=[CH:40][C:39]([F:42])=[CH:38][CH:37]=3)[C:21]([C:24]([C:27]3[CH:32]=[CH:31][C:30]([F:33])=[C:29]([O:34][CH3:35])[CH:28]=3)([CH3:26])[CH3:25])=[CH:22][N:23]=2)=[C:12]([Cl:43])[CH:11]=1)(=O)=O.[N-:44]=[N+:45]=[N-:46].[Na+]>CN(C=O)C>[N:44]([CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[C:14]([F:16])[C:13]([CH2:17][S:18][C:19]2[N:20]([C:36]3[CH:37]=[CH:38][C:39]([F:42])=[CH:40][CH:41]=3)[C:21]([C:24]([C:27]3[CH:32]=[CH:31][C:30]([F:33])=[C:29]([O:34][CH3:35])[CH:28]=3)([CH3:26])[CH3:25])=[CH:22][N:23]=2)=[C:12]([Cl:43])[CH:11]=1)=[N+:45]=[N-:46]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 86662232HCID 86662232, compound

Product 1

HCID 86662233HCID 86662233, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-(3-chloro-5-fluoro-4-((5-(2-(4-fluoro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-ylthio)methyl)phenoxy)propyl methanesulfonate (470 mg, 0.72 mmol) in DMF (3 mL) at 0° C. was added NaN3 (186 mg, 2.87 mmol). After stirring for 16 h, the mixture was partitioned in EtOAc (20 mL) and water (20 mL). The separated organic layer was washed with 1M HCl (10 mL) and water (10 mL) successively, dried over MgSO4, filtered and evaporated. The mixture was purified by column chromatography (EtOAc/Hex=1:3) to provide 2-(4-(3-azidopropoxy)-2-chloro-6-fluorobenzylthio)-5-(2-(4-fluoro-3-methoxyphenyl)-propan-2-yl)-1-(4-fluorophenyl)-1H-imidazole (344 mg, 80% yield) as a white foam. 1H NMR (400 MHz, CDCl3) δ 7.21 (s, 1H), 6.87 (dd, J=10.99, 8.49 Hz, 1H), 6.76 (t, J=8.49 Hz, 2H), 6.67 (s, 1H), 6.58 (dd, J=8.15, 2.15 Hz, 1H), 6.52-6.42 (m, 2H), 6.38-6.29 (m, 2H), 4.16 (t, J=4.34 Hz, 2H), 3.98 (t, J=5.89 Hz, 2H), 3.77 (d, J=5.67 Hz, 3H), 3.50 (t, J=6.51 Hz, 2H), 2.17 (s, 1H), 2.13-1.97 (m, 3H), 1.60 (s, 2H), 1.49 (s, 6H).

Workup

  1. customthe mixture was partitioned in EtOAc (20 mL)
  2. washThe separated 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 mixture was purified by column chromatography (EtOAc/Hex=1:3)

Sources & evidence

ORD record
ord-07d78ad443024880a639a77d17ada64e
Source dataset
uspto-grants-2014_07
Patent number
US08785488B2

Reaction notes

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