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4-Methylbenzaldehyde → 2-{(R)-1-[(3-Amino-propyl)-(4-methyl-benzyl)-amino]-but-3-ynyl}-7-chloro-3-phenylamino-3H-quinazolin-4-one

HRID 1517353
ノート
印刷プレビュー

反応式

HRID 1517353 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.[CH3:39][C:40]1[CH:47]=[CH:46][C:43]([CH:44]=O)=[CH:42][CH:41]=1>ClC(Cl)C.ClCCCl>[NH2:20][CH2:19][CH2:18][CH2:17][N:16]([CH2:39][C:40]1[CH:47]=[CH:46][C:43]([CH3:44])=[CH:42][CH:41]=1)[C@@H:12]([C:8]1[N:7]([NH:31][C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=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]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 77254-MethylbenzaldehydeHCID 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 251520012-{(R)-1-[(3-Amino-propyl)-(4-methyl-benzyl)-amino]-but-3-ynyl}-7-chloro-3-phenylamino-3H-quinazolin-4-one

試薬・触媒・溶媒 2

HCID 111,2-Dichloroethane溶媒HCID 6365
1,1-Dichloroethane
溶媒

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 dichloroethane (0.5 mL) was treated with respective aldehydes (in this case 4-methyl benzaldehyde, 0.25M solution in DCE, 0.8 mL, 0.2 μmol). The mixture was stirred at room temperature for 16 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 (14 mg, 24%). LCMS: m/e 500 [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-0b786d93ee0d40a1860b04ea90dc2b12
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…

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