3,4-bis(Benzyloxy)-6-(cyclohexylethynyl)pyridazine → HCID 178518809, compound

HRID 927134Notes

Reaction equation

HRID 927134 reaction equation
C([O:8][C:9]1[N:10]=[N:11][C:12]([C:23]#[C:24][CH:25]2[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)=[CH:13][C:14]=1[O:15]CC1C=CC=CC=1)C1C=CC=CC=1>CO.O1CCCC1>[CH:25]1([CH2:24][CH2:23][C:12]2[CH:13]=[C:14]([OH:15])[C:9](=[O:8])[NH:10][N:11]=2)[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1

Participants

4

Reactant 1

HCID 712700253,4-bis(Benzyloxy)-6-(cyclohexylethynyl)pyridazine2×

Product 1

HCID 178518809HCID 178518809, compoundYield 11%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Prepared as described for 4-hydroxy-6-(2-phenethyl)pyridazin-3(2H)-one (Example 1) from 3,4-bis(benzyloxy)-6-(cyclohexylethynyl)pyridazine (Intermediate 17) except that the reaction was carried out in a mixture of methanol and tetrahydrofuran (1:1). The resulting crude product was purified by preparative HPLC under acidic conditions. The solid obtained was recrystallised from methyl tert-butyl ether and ethyl acetate to afford 6-(2-cyclohexylethyl)-4-hydroxypyridazin-3(2H)-one as a cream solid (11% yield).

Workup

  1. customPrepared
  2. customThe resulting crude product was purified by preparative HPLC under acidic conditions
  3. customThe solid obtained
  4. customwas recrystallised from methyl tert-butyl ether and ethyl acetate

Sources & evidence

ORD record
ord-5af83f61287d420e86e7d2f00e1e5c56
Source dataset
uspto-grants-2016_03
Patent number
US09290456B2

Reaction notes

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