HCID 68452694, compound → HCID 68455662, compound
Reaction equation
[CH:1]1([NH:4][C:5](=[O:30])[C:6]2[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]([C:13]3[CH:14]=[C:15]4[C:20](=[CH:21][CH:22]=3)[C:19]([N:23]3[CH2:28][CH2:27][C:26](=[O:29])[CH2:25][CH2:24]3)=[N:18][N:17]=[CH:16]4)[CH:7]=2)[CH2:3][CH2:2]1.[CH:31]([Mg]Cl)([CH3:33])[CH3:32]>C1COCC1>[CH:1]1([NH:4][C:5](=[O:30])[C:6]2[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]([C:13]3[CH:14]=[C:15]4[C:20](=[CH:21][CH:22]=3)[C:19]([N:23]3[CH2:24][CH2:25][C:26]([OH:29])([CH:31]([CH3:33])[CH3:32])[CH2:27][CH2:28]3)=[N:18][N:17]=[CH:16]4)[CH:7]=2)[CH2:2][CH2:3]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
A mixture of N-cyclopropyl-4-methyl-3-(1-(4-oxopiperidin-1-yl)phthalazin-6-yl)benzamide (100 mg, 250 μmol) (Method A, followed by deprotection of the ketal) in 5 mL THF was stirred at −78° C. and treated with isopropylmagnesium chloride (250 μl, 499 μmol). The mixture was stirred at −78° C. warming to RT over 4 h. The mixture was quenched with 5 mL sat NH4Cl and extracted with dichloromethane (3×50 mL). The combined organics were dried over anhydrous Na2SO4, concentrated in vacuo and purified by silica gel chromatography eluting with 1-5% 2M ammonia methanol/dichloromethane to give the title compound. Found MS (ES+): 445(M+H)+.
Workup
- stirringThe mixture was stirred at −78° C.
- temperaturewarming to RT over 4 h
- customThe mixture was quenched with 5 mL
- extractionextracted with dichloromethane (3×50 mL)
- dry with materialThe combined organics were dried over anhydrous Na2SO4
- concentrationconcentrated in vacuo
- custompurified by silica gel chromatography
- washeluting with 1-5% 2M ammonia methanol/dichloromethane
Sources & evidence
- ORD record
- ord-2b2813c1994e40fc8334cdc76caed5cb
- Source dataset
- uspto-grants-2010_07
- Patent number
- US07759337B2
Reaction notes
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