Water → (S)-N-(3-(2-(Dimethylamino)ethoxy)-5-(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]pyrimidin-5-yl)phenyl)methanesulfonamide

HRID 1052753

反応式

HRID 1052753 の反応式
[OH:1][C:2]1[CH:3]=[C:4]([NH:37][S:38]([CH3:41])(=[O:40])=[O:39])[CH:5]=[C:6]([C:8]2[C:16]3[C:15]([NH:17][C@H:18]([C:20]4[N:25]([C:26]5[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=5)[C:24](=[O:32])[C:23]5=[C:33]([CH3:36])[CH:34]=[CH:35][N:22]5[N:21]=4)[CH3:19])=[N:14][CH:13]=[N:12][C:11]=3[NH:10][CH:9]=2)[CH:7]=1.C(=O)([O-])[O-].[Na+].[Na+].[Cl-].Cl[CH2:50][CH2:51][NH+:52]([CH3:54])[CH3:53].O>CN(C)C=O>[CH3:53][N:52]([CH3:54])[CH2:51][CH2:50][O:1][C:2]1[CH:3]=[C:4]([NH:37][S:38]([CH3:41])(=[O:39])=[O:40])[CH:5]=[C:6]([C:8]2[C:16]3[C:15]([NH:17][C@H:18]([C:20]4[N:25]([C:26]5[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=5)[C:24](=[O:32])[C:23]5=[C:33]([CH3:36])[CH:34]=[CH:35][N:22]5[N:21]=4)[CH3:19])=[N:14][CH:13]=[N:12][C:11]=3[NH:10][CH:9]=2)[CH:7]=1

参加物

6

反応物 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 20717(2-Chloroethyl)dimethylamine, chlorideHCID 901023362,3-d]Pyrimidin-5-yl]-5-oxidanyl-phenyl]methanesulfonamide

生成物 1

HCID 90102856(S)-N-(3-(2-(Dimethylamino)ethoxy)-5-(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]pyrimidin-5-yl)phenyl)methanesulfonamide収率 62.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

(S)—N-(3-Hydroxy-5-(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]pyrimidin-5-yl)phenyl)methanesulfonamide (6 mg, 0.01 mmol) was dissolved in 120 μl N,N-dimethylformamide. Sodium carbonate (8 mg, 0.07 mmol) and 2-chloro-N,N-dimethylethanaminium chloride (4 mg, 0.03 mmol) were added and the mixture was stirred at 50° C. overnight. The reaction was poured into water and extracted twice with ethyl acetate. The organics were combined and washed with brine, dried over sodium sulphate, filtered and evaporated under reduced pressure. The residue was purified using SP1® Purification System (0% to 100%, dichloromethane-dichloromethane/2-propanol 85:15) to give 4 mg (56% yield) of the title compound.

後処理

  1. extractionextracted twice with ethyl acetate
  2. washwashed with brine
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe residue was purified
  7. customSP1® Purification System (0% to 100%, dichloromethane-dichloromethane/2-propanol 85:15)

出典と根拠

ORDレコード
ord-3519fe54de6640d488dbb0549ce9a981
出典データセット
uspto-grants-2016_07
特許番号
US09388189B2

関連ノート

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