Sodium Azide → HCID 86662231, 화합물

HRID 1627300노트

반응식

HRID 1627300 반응식
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]

참가 물질

4

반응물 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

생성물 1

HCID 86662231HCID 86662231, 화합물수율 87.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-df5384d63def468ab38ad296f86d5a9d
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08785488B2

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