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Trifluoroacetic acid → (5S)-5-Methyl-5-({[4-[(2-methylpyrimidin-5-yl)ethynyl]-3,6-dihydropyridin-1(2H)-yl]sulfonyl}methyl)imidazolidine-2,4-dione

HRID 1669663
Notes
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Reaction equation

HRID 1669663 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 81531DiisopropylethylamineHCID 16738713(4S)-(4-methyl-2,5-dioxoimidazolidin-4-yl)methanesulphonyl chlorideHCID 86619012tert-Butyl 4-[(2-methylpyrimidin-5-yl)ethynyl]-3,6-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 11696764(5S)-5-Methyl-5-({[4-[(2-methylpyrimidin-5-yl)ethynyl]-3,6-dihydropyridin-1(2H)-yl]sulfonyl}methyl)imidazolidine-2,4-dione
Yield 30%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6228DimethylformamideSolvent

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

  1. customafter completion of the reaction the solvent
  2. customwas evaporated
  3. customdried
  4. stirringThe mixture was stirred for 10 min at 4° C.
  5. stirringstirred for 2 h at room temperature before the solvent
  6. customwas evaporated
  7. customThe product was purified by preparative HPLC

Sources & evidence

ORD record
ord-90128194508c418dab632454ca2f3c15
Source dataset
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07989620B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes