4-Ethyl-3-thiosemicarbazide → (S)-2-(1-((5-(5-(Ethylamino)-1,3,4-thiadiazol-2-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)ethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one

HRID 1052756ノート

反応式

HRID 1052756 の反応式
[CH3:1][C:2]1[CH:3]=[CH:4][N:5]2[C:10]=1[C:9](=[O:11])[N:8]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:7]([C@@H:18]([NH:20][C:21]1[C:22]3[C:29]([C:30](O)=O)=[CH:28][NH:27][C:23]=3[N:24]=[CH:25][N:26]=1)[CH3:19])=[N:6]2.[CH2:33]([NH:35][C:36]([NH:38][NH2:39])=[S:37])[CH3:34].O(Cl)Cl.[P+5]>O1CCOCC1>[CH2:33]([NH:35][C:36]1[S:37][C:30]([C:29]2[C:22]3[C:21]([NH:20][C@H:18]([C:7]4[N:8]([C:12]5[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=5)[C:9](=[O:11])[C:10]5=[C:2]([CH3:1])[CH:3]=[CH:4][N:5]5[N:6]=4)[CH3:19])=[N:26][CH:25]=[N:24][C:23]=3[NH:27][CH:28]=2)=[N:39][N:38]=1)[CH3:34]

参加物

5

反応物 3

HCID 15517804-Ethyl-3-thiosemicarbazideHCID 90102798HCID 90102798、化合物HCID 178479711HCID 178479711、化合物

生成物 1

HCID 136929378(S)-2-(1-((5-(5-(Ethylamino)-1,3,4-thiadiazol-2-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)ethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one収率 29%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
80 °C

実験手順

To a suspension of (S)-4-((1-(5-methyl-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethyl)amino)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylic acid (50 mg, 0.12 mmol) and N-ethylhydrazinecarbothioamide (21 mg, 0.18 mmol) in 1 ml 1,4-dioxane was added phosphorus (V) oxychloride (12.5 μL, 0.13 mmol). The mixture was stirred at 80° C. overnight. The solvent was evaporated and the residue was poured into water and ethyl acetate. The mixture was basified to pH 10 with sodium carbonate and extracted twice with ethyl acetate. The organics were combined and washed with water, brine, dried over sodium sulphate, filtered and evaporated under reduced pressure. The residue was precipitated using diethyl ether, filtered, washed with cold diethyl ether and dried in a vacuum oven to obtain 14 mg (29% yield) of the title compound.

後処理

  1. customThe solvent was evaporated
  2. additionthe residue was poured into water and ethyl acetate
  3. extractionextracted twice with ethyl acetate
  4. washwashed with water, brine
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customThe residue was precipitated
  9. filtrationfiltered
  10. washwashed with cold diethyl ether
  11. customdried in a vacuum oven

出典と根拠

ORDレコード
ord-b9eaa6a7dc594a07b816f44cd88535e3
出典データセット
uspto-grants-2016_07
特許番号
US09388189B2

反応ノート

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