3,4-bis(Benzyloxy)-6-{2-[3-chloro-4-(trifluoromethyl)phenyl]-ethynyl}pyridazine → 3,4-Bis(benzyloxy)-6-((3-chloro-4-(trifluoromethyl)phenyl)ethyl)-pyridazine

HRID 927183Notes

Reaction equation

HRID 927183 reaction equation
OC1C(=O)NN=C(CCC2C=CC=CC=2)C=1.[CH2:17]([O:24][C:25]1[N:26]=[N:27][C:28]([C:39]#[C:40][C:41]2[CH:46]=[CH:45][C:44]([C:47]([F:50])([F:49])[F:48])=[C:43]([Cl:51])[CH:42]=2)=[CH:29][C:30]=1[O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C1COCC1>[CH2:17]([O:24][C:25]1[N:26]=[N:27][C:28]([CH2:39][CH2:40][C:41]2[CH:46]=[CH:45][C:44]([C:47]([F:49])([F:48])[F:50])=[C:43]([Cl:51])[CH:42]=2)=[CH:29][C:30]=1[O:31][CH2:32][C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 712701623,4-bis(Benzyloxy)-6-{2-[3-chloro-4-(trifluoromethyl)phenyl]-ethynyl}pyridazine2×HCID 1785188083-Hydroxy-6-(2-Phenylethyl)pyridazin-4(1h)-One

Product 1

HCID 712705323,4-Bis(benzyloxy)-6-((3-chloro-4-(trifluoromethyl)phenyl)ethyl)-pyridazineYield 17%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Prepared as described for 4-hydroxy-6-(2-phenylethyl)pyridazin-3(2H)-one (Example 1) from 3,4-bis(benzyloxy)-6-{2-[3-chloro-4-(trifluoromethyl)phenyl]-ethynyl}pyridazine (Intermediate 75) except that THF was used as the solvent. The crude product was purified by reverse phase chromatography (eluting with 5-100% acetonitrile in water with acid modifier) to give a pale yellow solid. The solid was recrystallised from a mixture of methyl tert-butyl ether and ethyl acetate to afford 3,4-bis(benzyloxy)-6-((3-chloro-4-(trifluoromethyl)phenyl)ethyl)-pyridazine as a white solid (0.182 g, 17%).

Workup

  1. customPrepared
  2. customThe crude product was purified by reverse phase chromatography (eluting with 5-100% acetonitrile in water with acid modifier)
  3. customto give a pale yellow solid
  4. customThe solid was recrystallised from a mixture of methyl tert-butyl ether and ethyl acetate

Sources & evidence

ORD record
ord-5e7c3815ec7a4862a15be378816021dc
Source dataset
uspto-grants-2016_03
Patent number
US09290456B2

Reaction notes

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