1,4-Dichlorophthalazine → (R)-tert-butyl 4-(4-chlorophthalazin-1-yl)-3-methylpiperazine-1-carboxylate
Reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([Cl:12])=[N:4][N:3]=1.[CH3:13][C@H:14]1[NH:19][CH2:18][CH2:17][N:16]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:15]1>ClCCl>[Cl:12][C:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2]([N:19]2[CH2:18][CH2:17][N:16]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:15][C@H:14]2[CH3:13])=[N:3][N:4]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 120 °C
Procedure
1,4-dichlorophthalazine (5.00 g, 25.1 mmol) and (R)-tert-butyl 3-methylpiperazine-1-carboxylate (11.06 g, 55.2 mmol) were mixed intimately and placed in a flask under an Argon atmosphere. The flask was heated at 120° C. for approximately 16 hours, after which time LC/MS showed disappearance of the starting material. The reaction was cooled, taken up in dichloromethane (150 mL), and washed once with aqueous sodium bicarbonate (50% of saturated) and once with saturated sodium chloride solution. The organic phase was dried (MgSO4) and evaporated to give an orange oil. Chromatography over silica gel with a gradient of hexanes/0-10% acetone gave a pale yellow solid JK-1. MS (M+H)+=363.1.
Workup
- customplaced in a flask under an Argon atmosphere
- temperatureThe reaction was cooled
- washwashed once with aqueous sodium bicarbonate (50% of saturated) and once with saturated sodium chloride solution
- dry with materialThe organic phase was dried (MgSO4)
- customevaporated
- customto give an orange oil
Sources & evidence
- ORD record
- ord-00ab3d46dd16498db60ee8f4c60e06c4
- Source dataset
- uspto-grants-2012_04
- Patent number
- US08153633B2
Reaction notes
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