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 1627254ノート

反応式

HRID 1627254 の反応式
[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]

参加物

3

反応物 2

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

生成物 1

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

実験手順

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+).

後処理

  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)

出典と根拠

ORDレコード
ord-4f660114d0df4e30a2204541c2911ed7
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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