Nitrogen → HCID 178436325, compound

HRID 2247159Notes

Reaction equation

HRID 2247159 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([C:16]3[NH:20][C:19]4[CH:21]=[CH:22][C:23]([C:25]([NH2:27])=[O:26])=[CH:24][C:18]=4[N:17]=3)=[CH:12][CH:11]=2)=[CH2:9])=[CH:4][CH:3]=1.N#N>C(O)C.C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:10]2[CH:11]=[CH:12][C:13]([C:16]3[NH:20][C:19]4[CH:21]=[CH:22][C:23]([C:25]([NH2:27])=[O:26])=[CH:24][C:18]=4[N:17]=3)=[CH:14][CH:15]=2)[CH3:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 947NitrogenHCID 178436324HCID 178436324, compound

Product 1

HCID 178436325HCID 178436325, compoundYield 69.8%

Reagents, catalysts & solvents 1

HCID 21584252Ethanol ethylacetateSolvent

Procedure

A flask-containing a solution of 2-{4-[1-(4-chloro-phenyl)-vinyl]-phenyl}-1H-benzoimidazole-5-carboxylic acid amide (Example 41, 30 mg, 0.08 mmol) in 1:1 ethanol/ethyl acetate (6.0 mL) was charged with N2 and evacuated (3×). Palladium on carbon (10 wt %) was added to the solution, and the flask was charged with H2 and evacuated (3×), and then maintained at ˜1 atm H2 for 2.5 h. The flask was evacuated and then charged with N2. The reaction mixture was filtered through a pad of Celite®, which was washed with ethanol (50 mL), ethyl acetate (50 mL) and then methanol (2×50 mL). The filtrate was concentrated under reduced pressure. Purification of the residue by chromatography (silica gel, 1% methanol saturated with ammonia/9% methanol/CH2Cl2) afforded the title compound (21 mg, 68%). TLC (silica, 1% methanol saturated with ammonia/9/% methanol/CH2Cl2): Rf=0.35. MS (ESI+): mass calculated for C22H18ClN3O, 375.1, m/z found, 376.1. [M+H]+. 1H NMR (500 MHz, CD3OD): δ 8.16 (br s, 1H), 8.04 (d, J=8.4 Hz, 2H), 7.81 (d, J=8.3 Hz, 1H), 7.62 (br s, 1H), 7.43 (d, J=8.3 Hz, 2H), 7.30-7.26 (m, 4H), 4.27-4.24 (m, 1H), 1.67 (d, J=7.2 Hz, 3H).

Workup

  1. customevacuated (3×)
  2. additionPalladium on carbon (10 wt %) was added to the solution
  3. additionthe flask was charged with H2
  4. customevacuated (3×)
  5. temperaturemaintained at ˜1 atm H2 for 2.5 h
  6. customThe flask was evacuated
  7. additioncharged with N2
  8. filtrationThe reaction mixture was filtered through a pad of Celite®, which
  9. washwas washed with ethanol (50 mL), ethyl acetate (50 mL)
  10. concentrationThe filtrate was concentrated under reduced pressure
  11. customPurification of the residue by chromatography (silica gel, 1% methanol saturated with ammonia/9% methanol/CH2Cl2)

Sources & evidence

ORD record
ord-27fc0cc28beb4b7f8d14da7b63e58028
Source dataset
uspto-grants-2010_03
Patent number
US07687639B2

Reaction notes

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