Imidazole → HCID 9986138, compound

HRID 349275Notes

Reaction equation

HRID 349275 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[F:6][C:7]([F:43])([F:42])[C:8]1[CH:9]=[C:10]([CH:35]=[C:36]([C:38]([F:41])([F:40])[F:39])[CH:37]=1)[CH2:11][N:12]1[C:16](Cl)=[C:15]([C:18]([C:20]2[O:24][C:23]([CH:25]3[CH2:27][CH2:26]3)=[N:22][C:21]=2[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[Cl:34])=[O:19])[N:14]=[N:13]1.CCOC(C)=O>CS(C)=O>[F:41][C:38]([F:39])([F:40])[C:36]1[CH:35]=[C:10]([CH:9]=[C:8]([C:7]([F:6])([F:43])[F:42])[CH:37]=1)[CH2:11][N:12]1[C:16]([N:1]2[CH:5]=[CH:4][N:3]=[CH:2]2)=[C:15]([C:18]([C:20]2[O:24][C:23]([CH:25]3[CH2:26][CH2:27]3)=[N:22][C:21]=2[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[Cl:34])=[O:19])[N:14]=[N:13]1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 8857Ethyl AcetateHCID 86601233HCID 86601233, compound

Product 1

HCID 9986138HCID 9986138, compoundYield 88.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

Add imidazole (0.37 g, 5.44 mmol) to a solution of [1-(3,5-bis-trifluoromethyl-benzyl)-5-chloro-1H-[1,2,3]triazol-4-yl]-[4-(2-chloro-phenyl)-2-cyclopropyl-oxazol-5-yl]-methanone (0.16 g, 0.28 mmol) in DMSO (1.0 mL) and heat to 80° C. for 18 h. Dilute reaction mixture with EtOAc and wash with water and brine, then dry, filter, and concentrate. Purify by flash chromatography using a linear gradient of 30% to 70% EtOAc in hexane to give the title compound (0.15 g, 76%). MS (ES) 607.1 (M+H). 1H NMR (400 MHz, CHCl3) δ 7.88 (s, 1H), 7.61 (s, 1H) 7.51 (m, 3H), 7.21–7.33 (m, 4H), 6.92 (s, 1H), 5.43 (s, 2H), 2.20 (m, 1H), 1.17–1.31 (m, 4H).

Workup

  1. additionDilute
  2. washwash with water and brine
  3. customdry
  4. filtrationfilter
  5. concentrationconcentrate
  6. customPurify by flash chromatography

Sources & evidence

ORD record
ord-c841486ebdae4161bc9435635977a5c0
Source dataset
uspto-grants-2007_02
Patent number
US07179804B2

Reaction notes

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