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Triethylamine → 4-[(3-Bromophenyl)amino]-7-[3-(1-methylpiperidin-4-yl)propyloxy]-6-[(vinylcarbonyl)amino]quinazoline

HRID 1023293
ノート
印刷プレビュー

反応式

HRID 1023293 の反応式
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH2:13][CH2:14][CH2:15][CH:16]1[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][CH2:17]1)[N:8]=[CH:7][N:6]=[C:5]2[NH:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([Br:30])[CH:25]=1.C(N(CC)CC)C.[C:38](Cl)(=[O:41])[CH:39]=[CH2:40]>ClCCl.O1CCCC1>[Br:30][C:26]1[CH:25]=[C:24]([NH:23][C:5]2[C:4]3[C:9](=[CH:10][C:11]([O:12][CH2:13][CH2:14][CH2:15][CH:16]4[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][CH2:17]4)=[C:2]([NH:1][C:38]([CH:39]=[CH2:40])=[O:41])[CH:3]=3)[N:8]=[CH:7][N:6]=2)[CH:29]=[CH:28][CH:27]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 111906016-Amino-4-[(3-bromophenyl)amino]-7-[3-(1-methylpiperidin-4-yl)propyloxy]quinazoline

生成物 1

HCID 114098744-[(3-Bromophenyl)amino]-7-[3-(1-methylpiperidin-4-yl)propyloxy]-6-[(vinylcarbonyl)amino]quinazoline

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒
HCID 8028
Tetrahydrofuran
溶媒

反応条件

温度
-10 °C

実験手順

To a solution of 300 mg of 6-amino-4-[(3-bromophenyl)amino]-7-[3-(1-methylpiperidin-4-yl)propyloxy]quinazoline in 7 ml of dichloromethane are added 0.28 ml of triethylamine. The reaction mixture is cooled to about −10° C. in an ice/sodium chloride cooling bath. Then a solution of 59 μl of acrylic acid chloride in 1 ml of tetrahydrofuran is added dropwise within 10 minutes. The cooling bath is removed and the mixture is stirred for a further 15 minutes at ambient temperature. For working up, the reaction mixture is poured on to 20 ml of ice water and mixed with 2-3 ml of 2 N sodium hydroxide solution, whereupon a light-colored precipitate is formed. The precipitate is suction filtered, washed with cold water and dissolved in dichloromethane. The solution is dried over sodium sulfate and concentrated by evaporation. The resin-like crude product is purified by chromatography over a silica gel column with methylene chloride/methanol/concentrated ammonia solution (90:10:0.5). Yield: 118 mg (35% of theory); Rf value: 0.35 (silica gel, methylene chloride/methanol/concentrated aqueous ammonia solution=90:10:0.1); mass spectrum (ESI+): m/z=524, 526 [M+H]+.

後処理

  1. customThe cooling bath is removed
  2. additionthe reaction mixture is poured on to 20 ml of ice water
  3. additionmixed with 2-3 ml of 2 N sodium hydroxide solution, whereupon a light-colored precipitate
  4. customis formed
  5. filtrationfiltered
  6. washwashed with cold water
  7. dissolutiondissolved in dichloromethane
  8. dry with materialThe solution is dried over sodium sulfate
  9. concentrationconcentrated by evaporation
  10. customThe resin-like crude product is purified by chromatography over a silica gel column with methylene chloride/methanol/concentrated ammonia solution (90:10:0.5)

出典と根拠

ORDレコード
ord-bae2baedb3354cdca66ea762a50c8a3e
出典データセット
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08722694B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート