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Ethyl chloroformate → methyl {6-[(1-bromo-2-methylindolizin-3-yl)carbonyl]-2,4-dioxo-1,4-dihydroquinazolin-3(2H)-yl}acetate

HRID 1502211
ノート
印刷プレビュー

反応式

HRID 1502211 の反応式
Cl[C:2](OCC)=[O:3].[NH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]([C:16]2[N:24]3[C:19]([CH:20]=[CH:21][CH:22]=[CH:23]3)=[C:18]([Br:25])[C:17]=2[CH3:26])=[O:15])=[CH:10][C:9]=1[C:27]([NH:29][CH2:30][C:31]([O:33][CH3:34])=[O:32])=[O:28]>N1C=CC=CC=1.O1CCCC1.C(OCC)(=O)C>[Br:25][C:18]1[C:17]([CH3:26])=[C:16]([C:14]([C:11]2[CH:10]=[C:9]3[C:8](=[CH:13][CH:12]=2)[NH:7][C:2](=[O:3])[N:29]([CH2:30][C:31]([O:33][CH3:34])=[O:32])[C:27]3=[O:28])=[O:15])[N:24]2[C:19]=1[CH:20]=[CH:21][CH:22]=[CH:23]2
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 2

HCID 10928Ethyl chloroformateHCID 117776375methyl N-({2-amino-5-[(1-bromo-2-methylindolizin-3-yl)carbonyl]phenyl}carbonyl)glycinate

生成物 1

HCID 89618502methyl {6-[(1-bromo-2-methylindolizin-3-yl)carbonyl]-2,4-dioxo-1,4-dihydroquinazolin-3(2H)-yl}acetate収率 95%

試薬・触媒・溶媒 3

HCID 1049Pyridine溶媒HCID 8028Tetrahydrofuran
溶媒
HCID 8857Ethyl Acetate溶媒

実験手順

Ethyl chloroformate (1.3 mL; 13.5 mmol) is added dropwise to a solution of methyl N-({2-amino-5-[(1-bromo-2-methylindolizin-3-yl)carbonyl]phenyl}carbonyl)glycinate (2 g; 4.5 mmol) in 9 mL of pyridine at 0° C. After 15 min of stirring at ambient temperature, the reaction medium is concentrated to dryness and then diluted with ethyl acetate. The solution is washed with a 0.1 M hydrochloric acid solution and a saturated solution of sodium chloride, dried over sodium sulphate and concentrated to dryness. The yellow solid obtained is dissolved in 20 mL of anhydrous tetrahydrofuran and heated at reflux in the presence of diaza(1,3)bicyclo[5,4,0]undec-7-ene (1.35 mL; 9 mmol) for 1 h. The reaction medium is diluted with ethyl acetate, washed with a 0.1 M hydrochloric acid solution and a saturated solution of sodium chloride, dried over sodium sulphate and concentrated to dryness to give 2 g (95%) of a yellow powder.

後処理

  1. concentrationthe reaction medium is concentrated to dryness
  2. additiondiluted with ethyl acetate
  3. washThe solution is washed with a 0.1 M hydrochloric acid solution
  4. dry with materiala saturated solution of sodium chloride, dried over sodium sulphate
  5. concentrationconcentrated to dryness
  6. customThe yellow solid obtained
  7. temperatureheated
  8. washwashed with a 0.1 M hydrochloric acid solution
  9. dry with materiala saturated solution of sodium chloride, dried over sodium sulphate
  10. concentrationconcentrated to dryness

出典と根拠

ORDレコード
ord-911292f8937f40cf979c4de90d3047bd
出典データセット
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09206177B2

反応ノート

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