Triethylamine → N-(5-bromo-1,3-thiazol-2-yl)adamantane-1-carboxamide

HRID 255121

反応式

HRID 255121 の反応式
[Br:1][C:2]1[S:6][C:5]([NH2:7])=[N:4][CH:3]=1.[C:8]12([C:18](Cl)=[O:19])[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][CH:10]([CH2:11]3)[CH2:9]1)[CH2:15]2.C(N(CC)CC)C>O1CCCC1>[Br:1][C:2]1[S:6][C:5]([NH:7][C:18]([C:8]23[CH2:17][CH:12]4[CH2:11][CH:10]([CH2:16][CH:14]([CH2:13]4)[CH2:15]2)[CH2:9]3)=[O:19])=[N:4][CH:3]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 436002-Thiazolamine, 5-bromo-HCID 989151-Adamantanecarbonyl chloride

生成物 1

HCID 49760640N-(5-bromo-1,3-thiazol-2-yl)adamantane-1-carboxamide

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
80 °C

実験手順

A mixture of 5-bromothiazol-2-amine (3.0 g, 11.5 mmol), adamantane-1-carbonyl chloride (2.74 g, 13.8 mmol), triethylamine (3.2 mL, 23 mmol) and 4-di(methylamino)pyridine (1.1 g) in tetrahydrofuran (100 mL) was heated at 80° C. for 48 hours. The mixture was cooled to ambient temperature, concentrated, diluted with water and extracted with ethyl acetate. The organic extract was dried (Na2SO4), filtered and concentrated. Purification by flash chromatography (silica gel, 25% ethyl acetate/hexanes) afforded the title compound, MS (ESI) m/z 342 (M+H)+

後処理

  1. temperatureThe mixture was cooled to ambient temperature
  2. concentrationconcentrated
  3. additiondiluted with water
  4. extractionextracted with ethyl acetate
  5. extractionThe organic extract
  6. dry with materialwas dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification by flash chromatography (silica gel, 25% ethyl acetate/hexanes)

出典と根拠

ORDレコード
ord-bd8e77ef11af43c8866b7ef80c1fb69c
出典データセット
uspto-grants-2011_01
特許番号
US07875639B2

関連ノート

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