Imidazole → HCID 70656471, compound

HRID 872889Notes

Reaction equation

HRID 872889 reaction equation
Br[CH2:2][C:3]1[O:7][N:6]=[C:5]([C:8]([NH:10][C@@H:11]([CH3:27])[CH2:12][N:13]2[CH:17]=[CH:16][C:15]([C:18]3[CH:23]=[CH:22][C:21]([C:24]#[N:25])=[C:20]([Cl:26])[CH:19]=3)=[N:14]2)=[O:9])[CH:4]=1.[NH:28]1[CH:32]=[CH:31][N:30]=[CH:29]1>C(#N)C>[N:28]1([CH2:2][C:3]2[O:7][N:6]=[C:5]([C:8]([NH:10][C@@H:11]([CH3:27])[CH2:12][N:13]3[CH:17]=[CH:16][C:15]([C:18]4[CH:23]=[CH:22][C:21]([C:24]#[N:25])=[C:20]([Cl:26])[CH:19]=4)=[N:14]3)=[O:9])[CH:4]=2)[CH:32]=[CH:31][N:30]=[CH:29]1

Participants

4

Reactant 2

HCID 795ImidazoleHCID 67172292HCID 67172292, compound

Product 1

HCID 70656471HCID 70656471, compoundYield 13.81%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

(S)-5-(bromomethyl)-N-(1-(3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl)-propan-2-yl)isoxazole-3-carboxamide (0.328 g, 0.731 mmol) of Example 197(a) was dissolved in acetonitrile (10 ml) and imidazole (0.31 g, 4.55 mmol) dissolved in acetonitrile (3 ml) was added. The mixture was stirred at RT overnight. The mixture was evaporated, the residue dissolved in ethyl acetate and extracted with water. The organic phase was dried, filtered and evaporated. The product was purified by recrystallization from ethyl acetate. Yield 13.81%. 1H-NMR (400 MHz; DMSO-d6): δ 1.15 (d, 3H), 4.28-4.32 (m, 2H), 4.40-4.48 (m, 1H), 5.50 (s, 2H), 6.63 (s, 1H), 6.93 (d, 1H), 6.93-6.94 (m, 1H), 7.22-7.23 (m, 1H), 7.75-7.77 (m, 1H), 7.80 (d, 1H), 7.90 (dd, 1H), 7.96 (d, 1H), 8.07 (d, 1H), 8.80 (d, 1H).

Workup

  1. additionwas added
  2. customThe mixture was evaporated
  3. dissolutionthe residue dissolved in ethyl acetate
  4. extractionextracted with water
  5. customThe organic phase was dried
  6. filtrationfiltered
  7. customevaporated
  8. customThe product was purified by recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-15a02c840d35481191ec32a5ad2ddf51
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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