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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
ノート
印刷プレビュー

反応式

HRID 1669663 の反応式
[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]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 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

生成物 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
収率 30%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
4 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-90128194508c418dab632454ca2f3c15
出典データセット
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07989620B2

反応ノート

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