HCID 22379888, compound → HCID 22380016, compound

HRID 1988712Notes

Reaction equation

HRID 1988712 reaction equation
[CH2:1]([NH:4][C:5]([C:7]1[CH:31]=[CH:30][C:10]2[N:11]([CH2:28][CH3:29])[C:12]([CH2:14][C:15]3[N:16]([C:20]4[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:21]=4[F:27])[N:17]=[CH:18][CH:19]=3)=[N:13][C:9]=2[CH:8]=1)=[O:6])[C:2]#[CH:3]>C(O)(=O)C.C([O-])(=O)C.[Hg+2].C([O-])(=O)C>[CH2:28]([N:11]1[C:10]2[CH:30]=[CH:31][C:7]([C:5]3[O:6][C:2]([CH3:3])=[CH:1][N:4]=3)=[CH:8][C:9]=2[N:13]=[C:12]1[CH2:14][C:15]1[N:16]([C:20]2[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:21]=2[F:27])[N:17]=[CH:18][CH:19]=1)[CH3:29]

Participants

4

Reactant 1

HCID 22379888HCID 22379888, compound

Product 1

HCID 22380016HCID 22380016, compound

Reagents, catalysts & solvents 2

HCID 15337Mercuric acetateCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of crude N-propargyl 1-ethyl-2-{[2-(2,5-difluorophenyl)-pyrazol-3-yl]methyl}-1H-benzimidazole-5-carboxamide (450 mg) and mercury(II) acetate (1 eq) is heated at reflux in acetic acid (15 mL) for 6 h. The mixture is concentrated, saturated aqueous potassium carbonate added and extracted with ethyl acetate (3×). The combined organic layers were washed with water then with saturated aqueous sodium chloride, dried (MgSO4), concentrated, and triturated with ether to give 1-ethyl-2-{[2-(2,5-difluorophenyl)-pyrazol-3-yl]methyl}-5-(5-methyl-oxazol-2-yl)-1H-benzimidazole, which is converted to the hydrochloride salt in ethyl acetate. 1H NMR (d6 DMSO): δ 8.16 (s, 1H), 8.09-9.01 m. (2H), 7.78 (m, 1H), 7.62 (m, 1H), 7.49-7.45 (m, 3H), 7.04 (m, 1H), 6.56 (s, 1H), 4.70 (s, 2H), 4.36 (q, 2H), 2.41 (s, 3H), 1.21 (t, 3H). LCMS MH+ 420.5.

Workup

  1. temperatureis heated
  2. concentrationThe mixture is concentrated
  3. additionsaturated aqueous potassium carbonate added
  4. extractionextracted with ethyl acetate (3×)
  5. washThe combined organic layers were washed with water
  6. dry with materialwith saturated aqueous sodium chloride, dried (MgSO4)
  7. concentrationconcentrated
  8. customtriturated with ether

Sources & evidence

ORD record
ord-53d1bd9027544068b39ade34cfa86a76
Source dataset
uspto-grants-2010_01
Patent number
US07642267B2

Reaction notes

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