5-((5-(2-(3,4-Dichlorophenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-ylthio)methyl)-2-fluorobenzonitrile → 5-((5-(2-(3,4-Dichlorophenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-ylthio)methyl)-2-fluorobenzamide

HRID 1627254노트

반응식

HRID 1627254 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]([C:12]2[N:16]([C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=3)[C:15]([S:24][CH2:25][C:26]3[CH:27]=[CH:28][C:29]([F:34])=[C:30]([CH:33]=3)[C:31]#[N:32])=[N:14][CH:13]=2)([CH3:11])[CH3:10])[CH:5]=[CH:6][C:7]=1[Cl:8].C(O)(C(F)(F)F)=[O:36].OS(O)(=O)=O>>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]([C:12]2[N:16]([C:17]3[CH:18]=[CH:19][C:20]([F:23])=[CH:21][CH:22]=3)[C:15]([S:24][CH2:25][C:26]3[CH:27]=[CH:28][C:29]([F:34])=[C:30]([CH:33]=3)[C:31]([NH2:32])=[O:36])=[N:14][CH:13]=2)([CH3:11])[CH3:10])[CH:5]=[CH:6][C:7]=1[Cl:8]

참가 물질

3

반응물 2

HCID 667401155-((5-(2-(3,4-Dichlorophenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-ylthio)methyl)-2-fluorobenzonitrileHCID 86586073TFA sulfuric acid

생성물 1

HCID 667402815-((5-(2-(3,4-Dichlorophenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-ylthio)methyl)-2-fluorobenzamide수율 77%

실험 절차

A solution of 5-((5-(2-(3,4-dichlorophenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-ylthio)methyl)-2-fluorobenzonitrile (270 mg, 0.527 mmol) in TFA/H2SO4 (6 mL, 4:1, v/v) was heated at 65° C. for 8 h. The reaction mixture was cooled to room temperature, and the residue was partitioned into DCM and water. The separated organic layer was washed with satd NaHCO3, dried over MgSO4, filtered through Celite™, and concentrated. Purification by flash chromatography (DCM/EtOAc, 1:1) gave the title product (217 mg, 77%) as a white foam. 1H NMR (CDCl3, 400 MHz): δ 1.47 (s, 6H) 4.13 (s, 2H), 6.04 (br s, 1H), 6.36 (m, 2H), 6.65 (br s, 1H), 6.81 (m, 3H), 6.96 (s, 1H), 7.06 (m, 1H), 7.27 (m, 2H), 7.40 (m, 1H), 7.91 (m, 1H); MS (EI) m/z 532 (MH+).

후처리

  1. customthe residue was partitioned into DCM and water
  2. washThe separated organic layer was washed with satd NaHCO3
  3. dry with materialdried over MgSO4
  4. filtrationfiltered through Celite™
  5. concentrationconcentrated
  6. customPurification by flash chromatography (DCM/EtOAc, 1:1)

출처 및 근거

ORD 기록
ord-4f660114d0df4e30a2204541c2911ed7
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08785488B2

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