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4-Toluenesulfonyl chloride → N-(3-amino-propyl)-N-[(R)-1-(7-chloro-4-oxo-3-phenylamino-3,4-dihydro-quinazolin-2-yl)-but-3-ynyl]-4-methyl-benzenesulfonamide

HRID 1517352
ノート
印刷プレビュー

反応式

HRID 1517352 の反応式
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:38])[N:7]([NH:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[C:8]([C@H:12]([NH:16][CH2:17][CH2:18][CH2:19][N:20]3C(=O)C4C(=CC=CC=4)C3=O)[CH2:13][C:14]#[CH:15])=[N:9]2)=[CH:4][CH:3]=1.S(Cl)(Cl)(=O)=O.[CH3:44][C:45]1[CH:50]=[CH:49][C:48]([S:51](Cl)(=[O:53])=[O:52])=[CH:47][CH:46]=1>N1C=CC=CC=1.CC(N(C)C)=O.C(C#N)(C)=O>[NH2:20][CH2:19][CH2:18][CH2:17][N:16]([C@@H:12]([C:8]1[N:7]([NH:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:6](=[O:38])[C:5]2[C:10](=[CH:11][C:2]([Cl:1])=[CH:3][CH:4]=2)[N:9]=1)[CH2:13][C:14]#[CH:15])[S:51]([C:48]1[CH:49]=[CH:50][C:45]([CH3:44])=[CH:46][CH:47]=1)(=[O:53])=[O:52]
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

6

反応物 3

HCID 73974-Toluenesulfonyl chlorideHCID 24648Sulfuryl chlorideHCID 57695432(R)-2-{3-[1-(7-chloro-4-oxo-3-phenylamino-3,4-dihydro-quinazolin-2-yl)-but-3-ynylamino]-propyl}-isoindole-1,3-dione

生成物 1

HCID 25151810N-(3-amino-propyl)-N-[(R)-1-(7-chloro-4-oxo-3-phenylamino-3,4-dihydro-quinazolin-2-yl)-but-3-ynyl]-4-methyl-benzenesulfonamide

試薬・触媒・溶媒 2

HCID 1049
Pyridine
溶媒
HCID 131729853DMA AcCN溶媒

反応条件

温度
45 °C

実験手順

A solution of 2-{3-[(R)-1-(7-chloro-4-oxo-3-phenylamino-3,4-dihydro-quinazolin-2-yl)-but-3-ynylamino]-propyl}-isoindole-1,3-dione (52.6 mg, 0.10 μmol) in pyridine (0.5 mL) was treated with respective sulfonyl chloride (in this case 4-methyl benzenesulfonyl chloride, 0.25M solution in DMA/AcCN (1:1), 0.5 mL, 0.125 μmol). The mixture was stirred at 45° C. for 24 h. Solvent was removed under reduced pressure. Residue was taken in MeOH (1.0 mL) and treated with hydrazine (0.25 mL). Reaction mixture was stirred at room temperature for 16 h and solvent removed under reduced pressure. The product was purified with reverse phase chromatography to give final product. Yield (10.4 mg, 20%). LCMS: m/e 551 [M+H].

後処理

  1. customSolvent was removed under reduced pressure
  2. additiontreated with hydrazine (0.25 mL)
  3. customReaction mixture
  4. stirringwas stirred at room temperature for 16 h
  5. customsolvent removed under reduced pressure
  6. customThe product was purified with reverse phase chromatography

出典と根拠

ORDレコード
ord-fefdecdfb0fc44b1a68533e8dddc6f3b
出典データセット
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08232285B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート