Ethyl orthoformate → 4-Chloro-7-cyclopentyl-7H-imidazo[4,5-c]pyridazine

HRID 1846006Notes

Reaction equation

HRID 1846006 reaction equation
[Cl:1][C:2]1[C:3]([NH2:14])=[C:4]([NH:8][CH:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)[N:5]=[N:6][CH:7]=1.[CH2:15](OC(OCC)OCC)C>>[Cl:1][C:2]1[C:3]2[N:14]=[CH:15][N:8]([CH:9]3[CH2:13][CH2:12][CH2:11][CH2:10]3)[C:4]=2[N:5]=[N:6][CH:7]=1

Participants

3

Reactant 2

HCID 31214Ethyl orthoformateHCID 867232335-Chloro-N3-cyclopentylpyridazine-3,4-diamine

Product 1

HCID 867232344-Chloro-7-cyclopentyl-7H-imidazo[4,5-c]pyridazineYield 51%

Procedure

A mixture of 5-chloro-N-3-cyclopentylpyridazine-3,4-diamine (Preparation 12, 1.2 g, 5.64 mmol) and triethylorthoformate (10 mL) were heated to reflux for 1.5 hours. The reaction mixture was allowed to cool to room temperature, concentrated in vacuo and triturated with EtOAc (20 mL). The solid was filtered and the filtrate was reduced to dryness. The crude material was purified by silica gel column chromatography eluting with EtOAc to afford the title compound as a yellow solid in 51% yield, 902 mg.

Workup

  1. temperaturewere heated
  2. temperatureto reflux for 1.5 hours
  3. concentrationconcentrated in vacuo
  4. customtriturated with EtOAc (20 mL)
  5. filtrationThe solid was filtered
  6. customThe crude material was purified by silica gel column chromatography
  7. washeluting with EtOAc

Sources & evidence

ORD record
ord-76aa0d6429ff4453a36bf33c1fe2c3c8
Source dataset
uspto-grants-2015_02
Patent number
US08952008B2

Reaction notes

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