3,4-Bis(benzyloxy)-6-[(4-methoxycyclohex-1-en-1-yl)ethynyl]pyridazine → HCID 178489990, compound

HRID 927136Notes

Reaction equation

HRID 927136 reaction equation
C([O:8][C:9]1[N:10]=[N:11][C:12]([C:23]#[C:24][C:25]2[CH2:30][CH2:29][CH:28]([O:31][CH3:32])[CH2:27][CH:26]=2)=[CH:13][C:14]=1[O:15]CC1C=CC=CC=1)C1C=CC=CC=1>CO>[OH:15][C:14]1[C:9](=[O:8])[NH:10][N:11]=[C:12]([CH2:23][CH2:24][CH:25]2[CH2:30][CH2:29][CH:28]([O:31][CH3:32])[CH2:27][CH2:26]2)[CH:13]=1

Participants

3

Reactant 1

HCID 712703263,4-Bis(benzyloxy)-6-[(4-methoxycyclohex-1-en-1-yl)ethynyl]pyridazine2×

Product 1

HCID 178489990HCID 178489990, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Prepared as described for 4-hydroxy-6-(2-phenethyl)pyridazin-3(2H)-one (Example 1) from 3,4-bis(benzyloxy)-6-[(4-methoxycyclohex-1-en-1-yl)ethynyl]pyridazine (Intermediate 20) except that the reaction was carried out in methanol. The resulting crude product was purified by preparative HPLC under acidic conditions to afford 4-hydroxy-6-[2-(4-methoxycyclohexyl)ethyl]pyridazin-3(2H)-one (mixture of isomers) as a white solid (26% yield).

Workup

  1. customPrepared
  2. customThe resulting crude product was purified by preparative HPLC under acidic conditions

Sources & evidence

ORD record
ord-a30610e19d4249a09a8c01dac75f7faf
Source dataset
uspto-grants-2016_03
Patent number
US09290456B2

Reaction notes

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