Trifluoroacetic acid → (5S)-5-Methyl-5-({[4-[(2-methylpyrimidin-5-yl)ethynyl]-3,6-dihydropyridin-1(2H)-yl]sulfonyl}methyl)imidazolidine-2,4-dione
Reaction equation
[CH3:1][C:2]1[N:7]=[CH:6][C:5]([C:8]#[C:9][C:10]2[CH2:11][CH2:12][N:13](C(OC(C)(C)C)=O)[CH2:14][CH:15]=2)=[CH:4][N:3]=1.C(O)(C(F)(F)F)=O.C(N(C(C)C)C(C)C)C.[CH3:39][C@@:40]1([CH2:47][S:48](Cl)(=[O:50])=[O:49])[C:44](=[O:45])[NH:43][C:42](=[O:46])[NH:41]1>CCO.CN(C=O)C>[CH3:39][C@:40]1([CH2:47][S:48]([N:13]2[CH2:14][CH:15]=[C:10]([C:9]#[C:8][C:5]3[CH:6]=[N:7][C:2]([CH3:1])=[N:3][CH:4]=3)[CH2:11][CH2:12]2)(=[O:50])=[O:49])[NH:41][C:42](=[O:46])[NH:43][C:44]1=[O:45]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 4 °C
Procedure
tert-Butyl 4-[(2-methylpyrimidin-5-yl)ethynyl]-3,6-dihydropyridine-1(2H)-carboxylate was treated with TFA in EtOH and after completion of the reaction the solvent was evaporated and the mixture was freeze dried. The residue was taken up in DMF (1.5 mL) and the mixture was cooled to 4° C. N-Ethyldiisopropylamine (2.2 eq.) was added and the mixture was stirred for 20 minutes before adding [(4S)-4-methyl-2,5-dioxoimidazolidin-4-yl]methanesulfonyl chloride (Example 1f) (1.1 eq.) in DMF (1 mL). The mixture was stirred for 10 min at 4° C. and then stirred for 2 h at room temperature before the solvent was evaporated. The product was purified by preparative HPLC to give the title compound (0.022 g, 30%).
Workup
- customafter completion of the reaction the solvent
- customwas evaporated
- customdried
- stirringThe mixture was stirred for 10 min at 4° C.
- stirringstirred for 2 h at room temperature before the solvent
- customwas evaporated
- customThe product was purified by preparative HPLC
Sources & evidence
- ORD record
- ord-90128194508c418dab632454ca2f3c15
- Source dataset
- uspto-grants-2011_08
- Patent number
- US07989620B2
Reaction notes
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