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

HRID 1671554
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HRID 1671554 반응식
[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
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참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 1049Pyridine용매

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온도
80 °C

실험 절차

(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−).

후처리

  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)

출처 및 근거

ORD 기록
ord-568569a246f84bb69173ca67056c6bb0
출처 데이터셋
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07994324B2

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