6-Bromoquipazine → HCID 44219922、化合物

HRID 860010ノート

反応式

HRID 860010 の反応式
BrC1C=CC(S(O[CH2:12][C@@H:13]2[O:27][C:17]3=[C:18]4[C:23](=[CH:24][CH:25]=[C:16]3[O:15][CH2:14]2)[N:22]=[C:21]([CH3:26])[CH:20]=[CH:19]4)(=O)=O)=CC=1.[Br:28][C:29]1[CH:30]=[C:31]2[C:36](=[CH:37][CH:38]=1)[N:35]=[C:34]([N:39]1[CH2:44][CH2:43][NH:42][CH2:41][CH2:40]1)[CH:33]=[CH:32]2.C(=O)(O)[O-].[Na+]>CS(C)=O>[Br:28][C:29]1[CH:30]=[C:31]2[C:36](=[CH:37][CH:38]=1)[N:35]=[C:34]([N:39]1[CH2:40][CH2:41][N:42]([CH2:12][C@@H:13]3[O:27][C:17]4=[C:18]5[C:23](=[CH:24][CH:25]=[C:16]4[O:15][CH2:14]3)[N:22]=[C:21]([CH3:26])[CH:20]=[CH:19]5)[CH2:43][CH2:44]1)[CH:33]=[CH:32]2

参加物

5

反応物 3

HCID 1302616-BromoquipazineHCID 516892Sodium BicarbonateHCID 20624762[(2R)-8-methyl-2,3-dihydro[1,4]dioxino[2,3-f]quinolin-2-yl]methyl4-bromobenzenesulfonate

生成物 1

HCID 44219922HCID 44219922、化合物収率 39.3%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
75 °C

実験手順

To a solution of [(2R)-8-methyl-2,3-dihydro[1,4]dioxino[2,3-f]quinolin-2-yl]methyl 4 bromobenzene sulfonate (2.31 g, 5.13 mmol) in dimethylsulfoxide (123 mL) is added the 6-bromo-2-piperazin-1-yl-quinoline of Step B (1.5 g, 5.13 mmol) and the mixture is heated at 75° C. under nitrogen overnight. The mixture is poured into saturated aqueous sodium bicarbonate and extracted with ethyl acetate. The extracts are dried over anhydrous magnesium sulfate and evaporated to dryness. The residue is flash chromatographed on silica gel Merck-60 using a gradient of methanol (0.5–2%) in ethyl acetate-hexane (55:45) to provide the title compound as an off-white solid (1.02 g), m.p. 153–154° C.

後処理

  1. extractionextracted with ethyl acetate
  2. dry with materialThe extracts are dried over anhydrous magnesium sulfate
  3. customevaporated to dryness
  4. customchromatographed on silica gel Merck-60

出典と根拠

ORDレコード
ord-bb354057eb944558a4c9fedc147cdf05
出典データセット
uspto-grants-2006_12
特許番号
US07153849B2

反応ノート

読み込み中…