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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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2,6-dichloro-N'-hydroxybenzene-1-carboximidamide → 1-({4-[3-(2,6-Dichlorophenyl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl}carbonyl)-1,2,3,4-tetrahydroquinoline

HRID 551793
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HRID 551793 반응식
[N:1]1([C:11]([N:13]2[CH2:18][CH2:17][CH:16]([C:19](O)=[O:20])[CH2:15][CH2:14]2)=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.ON1C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C.[Cl:63][C:64]1[CH:69]=[CH:68][CH:67]=[C:66]([Cl:70])[C:65]=1[C:71](=[N:73]O)[NH2:72]>O.CN(C)C=O>[Cl:63][C:64]1[CH:69]=[CH:68][CH:67]=[C:66]([Cl:70])[C:65]=1[C:71]1[N:73]=[C:19]([CH:16]2[CH2:17][CH2:18][N:13]([C:11]([N:1]3[C:2]4[C:7](=[CH:6][CH:5]=[CH:4][CH:3]=4)[CH2:8][CH2:9][CH2:10]3)=[O:12])[CH2:14][CH2:15]2)[O:20][N:72]=1
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참가 물질

8

반응물 5

HCID 319562,6-dichloro-N'-hydroxybenzene-1-carboximidamideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 285131921-(3,4-dihydroquinolin-1(2H)-ylcarbonyl)piperidine-4-carboxylic acid

생성물 1

HCID 24852912
1-({4-[3-(2,6-Dichlorophenyl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl}carbonyl)-1,2,3,4-tetrahydroquinoline
수율 37.8%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

0.3 g of 1-(3,4-dihydroquinolin-1(2H)-ylcarbonyl)piperidine-4-carboxylic acid, 11 ml of dimethylformamide, 0.67 g of O-benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium tetrafluoroborate, 0.028 g of 1-hydroxybenzotriazole, 0.91 ml of diisopropylethylamine and then 0.32 g of 2,6-dichloro-N′-hydroxybenzenecarboximidamide are introduced into a 100 ml round-bottomed flask. The reaction medium is stirred at ambient temperature for 1 h 30 and then heated at 95° C. for 20 hours. Water is added and the mixture is extracted with ethyl acetate. The organic phase is washed three times with water and dried over sodium sulfate and the solvent is evaporated under reduced pressure. The residue is chromatographed on silica gel with a heptane/ethyl acetate gradient from 0/1 to 1/1. 0.18 g of 1-({4-[3-(2,6-dichlorophenyl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl}carbonyl)-1,2,3,4-tetrahydroquinoline is obtained.

후처리

  1. temperatureheated at 95° C. for 20 hours
  2. extractionthe mixture is extracted with ethyl acetate
  3. washThe organic phase is washed three times with water
  4. dry with materialdried over sodium sulfate
  5. customthe solvent is evaporated under reduced pressure
  6. customThe residue is chromatographed on silica gel with a heptane/ethyl acetate gradient from 0/1 to 1/1

출처 및 근거

ORD 기록
ord-dbda138097cc4f2faacfcf8f1e139397
출처 데이터셋
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07947834B2

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