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

HRID 1352222
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HRID 1352222 반응식
[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
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참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 6344Dichloromethane용매
HCID 8028
Tetrahydrofuran
용매

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온도
-10 °C

실험 절차

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]+.

후처리

  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)

출처 및 근거

ORD 기록
ord-cfb4dbd2787642a9a4565f9108938cdb
출처 데이터셋
uspto-grants-2007_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07220750B2

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