Hydrazine hydrate (1:1) → HCID 67216258, compound

HRID 1677581Notes

Reaction equation

HRID 1677581 reaction equation
O.NN.[CH3:4][O:5][C:6]1[CH:7]=[C:8]([C:15]([C:17]2[N:21]3[CH:22]=[CH:23][CH:24]=[CH:25][C:20]3=[C:19]([C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([O:32][CH3:33])[CH:27]=3)[N:18]=2)=[O:16])[CH:9]=[CH:10][C:11]=1[N+:12]([O-])=O>CO.[Pd]>[NH2:12][C:11]1[CH:10]=[CH:9][C:8]([C:15]([C:17]2[N:21]3[CH:22]=[CH:23][CH:24]=[CH:25][C:20]3=[C:19]([C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([O:32][CH3:33])[CH:27]=3)[N:18]=2)=[O:16])=[CH:7][C:6]=1[O:5][CH3:4]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 67216030HCID 67216030, compound

Product 1

HCID 67216258HCID 67216258, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

0.117 g of 10% Pd/C and then 0.27 ml (5.47 mmol) of hydrazine hydrate are added to 0.441 g (1 mmol) of (3-methoxy-4-nitrophenyl)[1-(3-methoxyphenyl)imidazo[1,5-a]pyridin-3-yl]methanone obtained in example 34 in 10 ml of methanol. The mixture is heated at 70° C. for 3 hours. The reaction medium is filtered through talc and the catalyst is washed with methanol. The filtrate is concentrated under reduced pressure. The residue is taken up in dichloromethane and washing is carried out with a saturated aqueous sodium chloride solution and then drying is carried out over sodium sulfate. After concentrating under reduced pressure, the residue is purified by column chromatography on silica gel, elution being carried out with dichloromethane. 0.354 g of a yellow foam is collected. The product is salified by addition of 1N hydrochloric acid in ethyl ether. After addition of ethyl ether, the precipitate is filtered off, washed with ethyl ether and then dried. A yellow solid is collected in the hydrochloride form. Melting point: 210° C.; 1H NMR (d6-DMSO): 3.86 (3H, s), 3.92 (3H, s), 6.88 (1H, d), 6.99 (1H, d), 7.22 (1H, t), 7.40-7.60 (5H, m), 8.14-8.27 (3H, m), 9.75 (1H, d)

Workup

  1. filtrationThe reaction medium is filtered through talc
  2. washthe catalyst is washed with methanol
  3. concentrationThe filtrate is concentrated under reduced pressure
  4. washwashing
  5. customdrying
  6. concentrationAfter concentrating under reduced pressure
  7. customthe residue is purified by column chromatography on silica gel, elution
  8. custom0.354 g of a yellow foam is collected
  9. additionThe product is salified by addition of 1N hydrochloric acid in ethyl ether
  10. additionAfter addition of ethyl ether
  11. filtrationthe precipitate is filtered off
  12. washwashed with ethyl ether
  13. customdried
  14. customA yellow solid is collected in the hydrochloride form

Sources & evidence

ORD record
ord-e732c778504d4f38ba404a0560c5b99c
Source dataset
uspto-grants-2011_08
Patent number
US08008321B2

Reaction notes

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