Diisopropylethylamine → 2-[6-(3-Methylazetidin-1-yl)pyrimidin-4-yl]-4-(1H-1,2,3-triazol-1-yl)-1,2-dihydro-3H-pyrazol-3-one
Reaction equation
Cl.[CH3:2][CH:3]1[CH2:6][NH:5][CH2:4]1.Cl.Cl[C:9]1[N:14]=[CH:13][N:12]=[C:11]([N:15]2[C:19](=[O:20])[C:18]([N:21]3[CH:25]=[CH:24][N:23]=[N:22]3)=[CH:17][NH:16]2)[CH:10]=1.C(N(C(C)C)C(C)C)C>O1CCCC1>[CH3:2][CH:3]1[CH2:6][N:5]([C:9]2[N:14]=[CH:13][N:12]=[C:11]([N:15]3[C:19](=[O:20])[C:18]([N:21]4[CH:25]=[CH:24][N:23]=[N:22]4)=[CH:17][NH:16]3)[CH:10]=2)[CH2:4]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
43 mg (0.4 mmol) of 3-methylazetidine hydrochloride, 100 mg (0.3 mmol) of the compound from Example 12A and 174 μl (130 mg, 1.0 mmol) of N-ethyl-N-(propan-2-yl)propane-2-amine are suspended in 2 ml of tetrahydrofuran and reacted in a single mode microwave (Emrys Optimizer) at 120° C. for 1.5 h. The reaction mixture is concentrated under reduced pressure, taken up in water with addition of aqueous 1 N sodium hydroxide solution (pH=9-10) and purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient). Yield: 25 mg (25% of theory)
Workup
- customreacted in a single mode microwave (Emrys Optimizer) at 120° C. for 1.5 h
- concentrationThe reaction mixture is concentrated under reduced pressure
- additiontaken up in water with addition of aqueous 1 N sodium hydroxide solution (pH=9-10)
- custompurified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient)
Sources & evidence
- ORD record
- ord-97b15334043246fe82147d897ad3c2cd
- Source dataset
- uspto-grants-2011_11
- Patent number
- US08067407B2
Reaction notes
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