Ammonium Hydroxide → HCID 178510373, compound

HRID 1868344Notes

Reaction equation

HRID 1868344 reaction equation
F[C:2](F)(F)[C:3]1[N:4]=[C:5]([C:8]2[C:12]([CH:13]=[CH:14][C:15]3[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=3)=[CH:11][NH:10][N:9]=2)[NH:6][CH:7]=1.[OH-].[NH4+:24]>>[N:17]1[CH:18]=[CH:19][CH:20]=[C:15]([CH:14]=[CH:13][C:12]2[C:8]([C:5]3[NH:6][CH:7]=[C:3]([C:2]#[N:24])[N:4]=3)=[N:9][NH:10][CH:11]=2)[CH:16]=1

Participants

3

Reactant 2

HCID 14923Ammonium HydroxideHCID 178506255HCID 178506255, compound

Product 1

HCID 178510373HCID 178510373, compound

Conditions

Temperature
60 °C

Procedure

A mixture of 3-{2-[3-(4-trifluoromethyl-1H-imidazol-2-yl)-1H-pyrazol-4-yl]-vinyl}-pyridine Compound 2 (50 mg, 0.164 mmole) and 5% aqueous ammonium hydroxide (20 mL) was stirred at 60° C. for 3 h until all of the starting material disappeared. After the solvent was removed in vacuo, the residue was dissolved in methanol and neutralized with several drops of 2M aqueous HCl to pH˜7. The solvent was evaporated and the crude compound was diluted with ethyl acetate and washed with water. The organic extracts were dried over MgSO4, filtered, and evaporated in vacuo. The product was purified by flash chromatography with 10% methanol/dichloromethane to give 2-[4-(2-pyridin-3-yl-vinyl)-1H-pyrazol-3-yl]-1H-imidazole-4-carbonitrile Compound 3 as a white solid (21.5 mg, 50%). 1H NMR (300 MHz, MeOD) δ 7.10 (d, J=16.5 Hz, 1H), 7.44 (dd, J=5, 7.8 Hz, 1H), 7.82 (d, J=14 Hz, 1H), 7.92 (s, 1H), 8.09 (d, J=7.7 Hz 1H), 8.18 (s, 1H), 8.37 (dd, J=1.5, 5 Hz, 1H), 8.63 (d, J=2 Hz, 1H); MS (ESI) m/z: 263.7 (M+H+).

Workup

  1. customAfter the solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in methanol and neutralized with several drops of 2M aqueous HCl to pH˜7
  3. customThe solvent was evaporated
  4. additionthe crude compound was diluted with ethyl acetate
  5. washwashed with water
  6. dry with materialThe organic extracts were dried over MgSO4
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. customThe product was purified by flash chromatography with 10% methanol/dichloromethane

Sources & evidence

ORD record
ord-2c19ebff65a94d188fcd5fa7d3d3ffa0
Source dataset
uspto-grants-2009_12
Patent number
US07635703B2

Reaction notes

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