4-Methylmorpholine → HCID 57742593, 화합물

HRID 911897노트

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HRID 911897 반응식
[Br:1][C:2]1[CH:3]=[C:4]([O:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:5]([NH:8][C:9]2[S:10][CH:11]=[C:12]([CH2:14][C:15]([O:20][CH3:21])([CH3:19])[C:16](O)=[O:17])[N:13]=2)=[N:6][CH:7]=1.C[N:30]1[CH2:35][CH2:34]O[CH2:32][CH2:31]1.ON1C2C=CC=CC=2N=N1.CCN=C=NCCCN(C)C.N1CCCC1>C(Cl)Cl.CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([O:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:5]([NH:8][C:9]2[S:10][CH:11]=[C:12]([CH2:14][C:15]([O:20][CH3:21])([CH3:19])[C:16]([N:30]3[CH2:35][CH2:34][CH2:32][CH2:31]3)=[O:17])[N:13]=2)=[N:6][CH:7]=1

참가 물질

8

반응물 5

HCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 31268PyrrolidineHCID 757711-HydroxybenzotriazoleHCID 57742924HCID 57742924, 화합물

생성물 1

HCID 57742593HCID 57742593, 화합물수율 81.6%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매2회

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온도
0 °C

실험 절차

In a 20 mL scintillation vial, 3-(2-(5-bromo-3-phenoxypyridin-2-ylamino)thiazol-4-yl)-2-methoxy-2-methylpropanoic acid (0.087 g, 0.187 mmol) was dissolved in CH2Cl2 (5 mL) and DMF (2 mL) and N-methylmorpholine (0.031 mL, 0.281 mmol), followed by addition of 1-hydroxybenzotriazole. The mixture was cooled to 0° C. and EDCI (0.0467 g, 0.244 mmol) was added. The resulting mixture was agitated for 30 minutes and pyrrolidine (0.020 g, 0.28 mmol) was added. The mixture was then agitated overnight, diluted with 50 mL of CH2Cl2 and washed with citric acid solution and sodium bicarbonate solution, dried and evaporated to give crude product which was purified by chromatography on silica gel, eluting with 50-70% ethyl acetate/Hexane, to provide the title compound (0.079 g, 79% yield) as white solid. 1H NMR (DMSO-d6 δ 1.23 (s, 3H), 1.66-1.80 (m, 4H), 3.03-3.63 (m, 9H), 7.01 (m, 1H), 7.16-7.46 (m, 7H), 8.25 (s, 1H).

후처리

  1. stirringThe mixture was then agitated overnight
  2. washwashed with citric acid solution and sodium bicarbonate solution
  3. customdried
  4. customevaporated
  5. customto give crude product which
  6. customwas purified by chromatography on silica gel
  7. washeluting with 50-70% ethyl acetate/Hexane

출처 및 근거

ORD 기록
ord-17f9802b5297499f9635c4dd04d29fd8
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08022223B2

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