Dichloromethane → HCID 67188173、化合物

HRID 551818ノート

反応式

HRID 551818 の反応式
[N:1]1([C:11]2[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][CH:12]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][CH2:3][CH2:2]1.ClCCl.ClC(Cl)(O[C:28](=[O:34])OC(Cl)(Cl)Cl)Cl.Cl.Cl.[NH:38]1[CH2:42][CH2:41][CH:40]([C:43]2[CH:44]=[N:45][NH:46][CH:47]=2)[CH2:39]1>C(N(CC)CC)C>[NH:45]1[CH:44]=[C:43]([CH:40]2[CH2:41][CH2:42][N:38]([C:28]([N:4]3[C:5]4[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=4)[N:1]([C:11]4[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][CH:12]=4)[CH2:2][CH2:3]3)=[O:34])[CH2:39]2)[CH:47]=[N:46]1

参加物

6

反応物 4

HCID 6344DichloromethaneHCID 94429TriphosgeneHCID 671872294-(pyrrolidin-3-yl)-1H-pyrazole dihydrochlorideHCID 67190045methyl 4-(3,4-dihydroquinoxalin-1(2H)-yl)benzoate

生成物 1

HCID 67188173HCID 67188173、化合物収率 242.7%

試薬・触媒・溶媒 1

HCID 8471Triethylamine溶媒2 回

反応条件

温度
4 °C

実験手順

2.7 g of methyl 4-(3,4-dihydroquinoxalin-1(2H)-yl)benzoate and 50 ml of dichloromethane are introduced into a three-necked flask equipped with a magnetic stirrer and placed under an inert atmosphere. After cooling to 4° C., 4.2 ml of triethylamine and 1.19 g of triphosgene are successively added. The reaction medium is stirred at ambient temperature for 4 h. 2.11 g of 4-(pyrrolidin-3-yl)-1H-pyrazole dihydrochloride and 1.4 ml of triethylamine are then introduced and the mixture is stirred at ambient temperature for 18 h. The reaction medium is washed with a saturated aqueous sodium hydrogencarbonate solution; the organic phase is dried over sodium sulfate and concentrated under reduced pressure. The residue is chromatographed on silica gel eluted with a gradient of methanol from 1.5% to 3% in dichloromethane. 4.2 g of methyl 4-[4-{[3-(1H-pyrazol-4-yl)pyrrolidin-1-yl]carbonyl}-3,4-dihydroquinoxalin-1(2H)-yl]benzoate are obtained.

後処理

  1. customequipped with a magnetic stirrer
  2. stirringthe mixture is stirred at ambient temperature for 18 h
  3. washThe reaction medium is washed with a saturated aqueous sodium hydrogencarbonate solution
  4. dry with materialthe organic phase is dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is chromatographed on silica gel
  7. washeluted with a gradient of methanol from 1.5% to 3% in dichloromethane

出典と根拠

ORDレコード
ord-e8b97dc7a10041cfaf52031ab8302a07
出典データセット
uspto-grants-2011_05
特許番号
US07947834B2

反応ノート

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