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1,2-Ethanediamine, N1,N1,N2-trimethyl- → (2S,4S)-1-acryloyl-4-(4-amino-5-((3,5-dimethoxyphenyl)ethynyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-N-(2-(dimethylamino)ethyl)-N-methylpyrrolidine-2-carboxamide

HRID 516182
ノート
印刷プレビュー

反応式

HRID 516182 の反応式
[NH2:1][C:2]1[C:3]2[C:10]([C:11]#[C:12][C:13]3[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[C:15]([O:21][CH3:22])[CH:14]=3)=[CH:9][N:8]([C@@H:23]3[CH2:27][N:26]([C:28](OC(C)(C)C)=[O:29])[C@H:25]([C:35](O)=[O:36])[CH2:24]3)[C:4]=2[N:5]=[CH:6][N:7]=1.CN(C(ON1N=N[C:48]2C=CC=C[C:47]1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[CH3:60][N:61]([CH3:66])[CH2:62][CH2:63][NH:64][CH3:65].CCN(C(C)C)C(C)C>C(#N)C.O.C(OCC)(=O)C>[C:28]([N:26]1[CH2:27][C@@H:23]([N:8]2[C:4]3[N:5]=[CH:6][N:7]=[C:2]([NH2:1])[C:3]=3[C:10]([C:11]#[C:12][C:13]3[CH:14]=[C:15]([O:21][CH3:22])[CH:16]=[C:17]([O:19][CH3:20])[CH:18]=3)=[CH:9]2)[CH2:24][C@H:25]1[C:35]([N:64]([CH2:63][CH2:62][N:61]([CH3:66])[CH3:60])[CH3:65])=[O:36])(=[O:29])[CH:47]=[CH2:48]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 673381,2-Ethanediamine, N1,N1,N2-trimethyl-HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 89870887(2S,4S)-4-(4-amino-5-((3,5-dimethoxyphenyl)ethynyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid

生成物 1

HCID 90353248
(2S,4S)-1-acryloyl-4-(4-amino-5-((3,5-dimethoxyphenyl)ethynyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-N-(2-(dimethylamino)ethyl)-N-methylpyrrolidine-2-carboxamide

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6342Acetonitrile溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A solution of (2S,4S)-4-(4-amino-5-((3,5-dimethoxyphenyl)ethynyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid (25.4 mg) obtained in Example 68 (Step 1), TBTU (17.7 mg), N,N,N′-trimethylethane-1,2-diamine (13 μl), and DIPEA (26 μl) in acetonitrile (3 ml) was stirred at room temperature for 1 hour. Ethyl acetate and water were added to separate the organic layer. The organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The resulting residue was purified by basic silica gel column chromatography (developing solvent: chloroform/methanol) to obtain the title compound as a light-yellow, amorphous substance (3 mg). Physical properties: m/z [M+H]+ 592.4

後処理

  1. customto separate the organic layer
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe resulting residue was purified by basic silica gel column chromatography (developing solvent: chloroform/methanol)

出典と根拠

ORDレコード
ord-f3fe99577fd64583923f4c9b2304dd92
出典データセット
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09108973B2

反応ノート

読み込み中…

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