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

HRID 1846056Notes

Reaction equation

HRID 1846056 reaction equation
[Cl:1][C:2]1[C:3]([NH2:12])=[C:4]([NH:8][CH:9]2[CH2:11][CH2:10]2)[N:5]=[N:6][CH:7]=1.[CH2:13](OC(OCC)OCC)C>>[Cl:1][C:2]1[C:3]2[N:12]=[CH:13][N:8]([CH:9]3[CH2:10][CH2:11]3)[C:4]=2[N:5]=[N:6][CH:7]=1

Participants

3

Reactant 2

HCID 31214Ethyl orthoformateHCID 867232775-Chloro-N3-cyclopropylpyridazine-3,4-diamine

Product 1

HCID 867232784-Chloro-7-cyclopropyl-7H-imidazo[4,5-c]pyridazineYield 48%

Procedure

A mixture of 5-chloro-N-3-cyclopropylpyridazine-3,4-diamine (Preparation 90, 10.0 g, 54 mmol) and triethylorthoformate (120 mL) were heated to reflux for 3 hours. The reaction mixture was concentrated in vacuo and the residue was purified by silica gel column chromatography eluting with CH2Cl2:MeOH 98:2 to afford the title compound as a brown solid in 48% yield, 5 g.

Workup

  1. temperaturewere heated
  2. temperatureto reflux for 3 hours
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. customthe residue was purified by silica gel column chromatography
  5. washeluting with CH2Cl2:MeOH 98:2

Sources & evidence

ORD record
ord-0a0fbb9b55924b23a84bb909be399f6b
Source dataset
uspto-grants-2015_02
Patent number
US08952008B2

Reaction notes

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