Sodium Azide → HCID 86662231、化合物

HRID 1627300ノート

反応式

HRID 1627300 の反応式
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]

参加物

4

反応物 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

生成物 1

HCID 86662231HCID 86662231、化合物収率 87.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-df5384d63def468ab38ad296f86d5a9d
出典データセット
uspto-grants-2014_07
特許番号
US08785488B2

反応ノート

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