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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
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HRID 1517352 반응식
[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]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 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

생성물 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

시약·촉매·용매 2

HCID 1049
Pyridine
용매
HCID 131729853DMA AcCN용매

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온도
45 °C

실험 절차

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].

후처리

  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

출처 및 근거

ORD 기록
ord-fefdecdfb0fc44b1a68533e8dddc6f3b
출처 데이터셋
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08232285B2

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