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3-Methoxypropanoyl chloride → N-[2-((R)-Indan-1-ylamino)-quinolin-5-yl]-3-methoxy-propionamide

HRID 1671554
ノート
印刷プレビュー

反応式

HRID 1671554 の反応式
[C@H:1]1([NH:10][C:11]2[CH:20]=[CH:19][C:18]3[C:17]([NH2:21])=[CH:16][CH:15]=[CH:14][C:13]=3[N:12]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[CH3:22][O:23][CH2:24][CH2:25][C:26](Cl)=[O:27]>N1C=CC=CC=1.CN(C)C1C=CN=CC=1>[C@H:1]1([NH:10][C:11]2[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[CH:16][C:17]=3[NH:21][C:26](=[O:27])[CH2:25][CH2:24][O:23][CH3:22])[N:12]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1
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

5

反応物 2

HCID 27597283-Methoxypropanoyl chlorideHCID 44219082(R)-N2-Indan-1-yl-quinoline-2,5-diamine

生成物 1

HCID 44219235N-[2-((R)-Indan-1-ylamino)-quinolin-5-yl]-3-methoxy-propionamide

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 1049Pyridine溶媒

反応条件

温度
80 °C

実験手順

(R)—N2-Indan-1-yl-quinoline-2,5-diamine (150 mg, 0.55 mmol) was dissolved in 3 mL pyridine and 3-methoxypropionyl chloride (70 mg, 0.0.57 mmol) and 4-dimethylamino pyridine (3 mg, 0.02 mmol) were added. The reaction mixture was stirred at 80° C. overnight and quenched by addition of 50 mL water and acetic acid until pH 5. The mixture was extracted three times with ethyl acetate (50 mL each). The organic phases ware pooled, dried with sodium sulfate, filtered and evaporated. The residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 100:0→0:100 gradient). The title compound was obtained as a brown solid (59 mg, 30%), MS: m/e=362.4 (M+H−).

後処理

  1. customquenched by addition of 50 mL water and acetic acid until pH 5
  2. extractionThe mixture was extracted three times with ethyl acetate (50 mL each)
  3. dry with materialdried with sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 100:0→0:100 gradient)

出典と根拠

ORDレコード
ord-568569a246f84bb69173ca67056c6bb0
出典データセット
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07994324B2

反応ノート

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