4-Methylmorpholine → HCID 57742593、化合物

HRID 911897ノート

反応式

HRID 911897 の反応式
[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

参加物

8

反応物 5

HCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 31268PyrrolidineHCID 757711-HydroxybenzotriazoleHCID 57742924HCID 57742924、化合物

生成物 1

HCID 57742593HCID 57742593、化合物収率 81.6%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-17f9802b5297499f9635c4dd04d29fd8
出典データセット
uspto-grants-2011_09
特許番号
US08022223B2

反応ノート

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