Hydrazine hydrate (1:1) → HCID 178507894, compound

HRID 1110846Notes

Reaction equation

HRID 1110846 reaction equation
Cl[C:2]1[CH:7]=[C:6]([N:8]([CH2:14][CH2:15][CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)C(=O)OCC)[N:5]=[C:4]2[NH:22][CH:23]=[N:24][C:3]=12.O.[NH2:26]N>>[NH2:26][C:2]1[CH:7]=[C:6]([NH:8][CH2:14][CH2:15][CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)[N:5]=[C:4]2[NH:22][CH:23]=[N:24][C:3]=12

Participants

3

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 178473476HCID 178473476, compound

Product 1

HCID 178507894HCID 178507894, compound

Procedure

A mixture of 100 mg ethyl N-(7-chloro-3H-imidazo[4,5-b]pyridin-5-yl)-N-(2-cyclohexylethyl)-carbamate in 1 ml of hydrazine monohydrate is heated at 120° in a sealed tube for 24 hours. The solvent is evaporated in vacuo and 5 ml of methanol saturated with ammonia is added to the residue. This is followed by 0.1 ml of a suspension of Raney nickel in methanol saturated with ammonia. The mixture is heated in a sealed tube at 130° for 24 hours. The catalyst is filtered and washed with methanol, and the solvents are evaporated in vacuo to give a residue which is purified by flash chromatography (10% methanol saturated with ammonia/methylene chloride) to give 7-amino-N-(2-cyclohexylethyl)-3H-imidazo[4,5-b]pyridin-5-amine.

Workup

  1. temperatureis heated at 120° in a sealed tube for 24 hours
  2. customThe solvent is evaporated in vacuo and 5 ml of methanol saturated with ammonia
  3. additionis added to the residue
  4. temperatureThe mixture is heated in a sealed tube at 130° for 24 hours
  5. filtrationThe catalyst is filtered
  6. washwashed with methanol
  7. customthe solvents are evaporated in vacuo
  8. customto give a residue which
  9. customis purified by flash chromatography (10% methanol saturated with ammonia/methylene chloride)

Sources & evidence

ORD record
ord-9882a27ccb6c43ba953c25a39e159bce
Source dataset
uspto-grants-1990_12
Patent number
US04977144

Reaction notes

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