4-Methoxybenzyl alcohol → HCID 57977974, compound

HRID 1865840Notes

Reaction equation

HRID 1865840 reaction equation
Cl[C:2]1[C:3]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)=[C:4]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)[C:5]2[N:6]([CH:8]=[N:9][N:10]=2)[N:7]=1.[CH3:25][O:26][C:27]1[CH:34]=[CH:33][C:30]([CH2:31][OH:32])=[CH:29][CH:28]=1.C(N=P1(N(CC)CC)N(C)CCCN1C)(C)(C)C>C1COCC1>[Cl:24][C:21]1[CH:22]=[CH:23][C:18]([C:3]2[C:2]([O:32][CH2:31][C:30]3[CH:33]=[CH:34][C:27]([O:26][CH3:25])=[CH:28][CH:29]=3)=[N:7][N:6]3[CH:8]=[N:9][N:10]=[C:5]3[C:4]=2[C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 77384-Methoxybenzyl alcoholHCID 35138512-((1,1-Dimethylethyl)imino)-N,N-diethylhexahydro-1,3-dimethyl-2lambda5-1,3,2-diazaphosphorin-2-amineHCID 57978002HCID 57978002, compound

Product 1

HCID 57977974HCID 57977974, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To round bottom flask was added 6-chloro-7,8-bis(4-chlorophenyl)-[1,2,4]triazolo[4,3-b]pyridazine (37.6 mg, 0.10 mmol), 4-methyoxybenzyl alcohol (0.15 mmol), THF (1 ml) and 2-tert-butylimino-2-diethylamino-1,3-dimethyl-perhydro-1,3,2-diazaphosphorine (BEMP) (30 mg, 0.11 mmol). The reaction was heated to 50° C. and stirred at this temperature for 40 hrs. The solvent was removed and the residue was purified using preparative HPLC to give pure product 7,8-bis(4-chlorophenyl)-6-(4-methoxybenzyloxy)-[1,2,4]triazolo[4,3-b]pyridazine as a solid. HPLC retention time (method C) 7.91 min; LCMS (M+H)=477.10.

Workup

  1. customThe solvent was removed
  2. customthe residue was purified

Sources & evidence

ORD record
ord-addbcf1f86be493db0c49d532eaee9dc
Source dataset
uspto-grants-2009_12
Patent number
US07629342B2

Reaction notes

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