p-Toluenesulfonic acid → (R)-(4-(4-(4-(2-hydroxyethyl)phenyl)phthalazin-1-yl)-3-methylpiperazin-1-yl)(phenyl)methanone

HRID 1689981Notes

Reaction equation

HRID 1689981 reaction equation
[CH3:1][C@H:2]1[N:7]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]([C:18]3[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][O:26]C4CCCCO4)=[CH:20][CH:19]=3)=[N:10][N:9]=2)[CH2:6][CH2:5][N:4]([C:33]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[O:34])[CH2:3]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C([O-])([O-])=O.[K+].[K+]>CO>[OH:26][CH2:25][CH2:24][C:21]1[CH:22]=[CH:23][C:18]([C:11]2[C:12]3[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:8]([N:7]3[CH2:6][CH2:5][N:4]([C:33]([C:35]4[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=4)=[O:34])[CH2:3][C@H:2]3[CH3:1])=[N:9][N:10]=2)=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 11430Potassium CarbonateHCID 57581517((R)-3-methyl-4-(4-(4-(2-(tetrahydro-2H-pyran-2-yloxy)ethyl)phenyl)phthalazin-1-yl)piperazin-1-yl)(phenyl)methanone

Product 1

HCID 57581513(R)-(4-(4-(4-(2-hydroxyethyl)phenyl)phthalazin-1-yl)-3-methylpiperazin-1-yl)(phenyl)methanone

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

((R)-3-methyl-4-(4-(4-(2-(tetrahydro-2H-pyran-2-yloxy)ethyl)phenyl)phthalazin-1-yl)piperazin-1-yl)(phenyl)methanone (122 mg, 0.227 mmol) 83 and p-toluenesulfonic acid (130 mg, 0.682 mmol) were dissolved in methanol (4 mL) and stirred at rt for 1.5 hours. The reaction was added to 35 mL aqueous K2CO3 (10%) and extracted three times with 30 mL portions of dichloromethane. The combined organic extracts were dried over MgSO4 and evaporated to give a pale yellow solid, compound 84. MS (M+H)+=453.2.

Workup

  1. extractionextracted three times with 30 mL portions of dichloromethane
  2. dry with materialThe combined organic extracts were dried over MgSO4
  3. customevaporated

Sources & evidence

ORD record
ord-cfd8a5f3659f46aeac91dc902a932328
Source dataset
uspto-grants-2012_04
Patent number
US08153633B2

Reaction notes

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