Hydrazine → HCID 11461922, compound

HRID 1272092Notes

Reaction equation

HRID 1272092 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:26][CH3:27])=[C:6]([C:8]2[N:13]=[C:12]([NH:14]C(=O)C)[CH:11]=[C:10]([NH:18][C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=3)[CH:9]=2)[CH:7]=1.NN>C(O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:26][CH3:27])=[C:6]([C:8]2[N:13]=[C:12]([NH2:14])[CH:11]=[C:10]([NH:18][C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=3)[CH:9]=2)[CH:7]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 11773465HCID 11773465, compound

Product 1

HCID 11461922HCID 11461922, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of N-[6-(5-chloro-2-methoxy-phenyl)-4-p-tolylamino-pyridin-2-yl]-acetamide (15 mg, 0.039) prepared according to Example 5 in ethanol (4 ml) was added hydrazine (0.01 ml). After heating under reflux for 3 hours, the mixture was concentrated under reduced pressure. The residue was treated with water (40 ml) and extracted with ethyl acetate (50 ml). The organic extract was dried over sodium sulfate, filtered, and concentrated under reduced pressure to give the title compound (6 mg, 45% yield). 1H NMR (acetone-d6) δ 2.31 (s, 3H, CH3), 3.90 (s, 3H, CH3), 5.40 (s, 2H, NH2), 6.16 (t, 1H, J=2.0 Hz, Ar), 7.04 (bs, 1H, Ar), 7.09 (t, 1H, J=8.8 Hz, Ar), 7.17 (bs, 4H, Ar), 7.32 (dd, 1H, J=8.8 Hz, J=2.8 Hz, Ar), 7.72 (s, 1H, NH), 7.93 (d, 1H, J=2.8 Hz, Ar).

Workup

  1. temperatureAfter heating
  2. temperatureunder reflux for 3 hours
  3. concentrationthe mixture was concentrated under reduced pressure
  4. additionThe residue was treated with water (40 ml)
  5. extractionextracted with ethyl acetate (50 ml)
  6. extractionThe organic extract
  7. dry with materialwas dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-377eee2a2609413b80a71df1f8ffc957
Source dataset
uspto-grants-2007_04
Patent number
US07208507B2

Reaction notes

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