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

HRID 1469934

反応式

HRID 1469934 の反応式
Br.[NH2:2][C:3]1[S:4][C:5]([Br:8])=[CH:6][N:7]=1.[C:9]12([C:19](Cl)=[O:20])[CH2:18][CH:13]3[CH2:14][CH:15]([CH2:17][CH:11]([CH2:12]3)[CH2:10]1)[CH2:16]2.C(N(CC)CC)C>CN(C)C1C=CN=CC=1.C1COCC1.C(OCC)(=O)C>[Br:8][C:5]1[S:4][C:3]([NH:2][C:19]([C:9]23[CH2:18][CH:13]4[CH2:12][CH:11]([CH2:17][CH:15]([CH2:14]4)[CH2:16]2)[CH2:10]3)=[O:20])=[N:7][CH:6]=1

参加物

7

反応物 3

HCID 8471TriethylamineHCID 989151-Adamantanecarbonyl chlorideHCID 27238485-Bromothiazol-2-amine monohydrobromide

生成物 1

HCID 49760640N-(5-bromo-1,3-thiazol-2-yl)adamantane-1-carboxamide収率 65%

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

A mixture of 2-amino-5-bromothiazole monohydrobromide (3.00 g, 11.5 mmol), 1-adamantanecarbonyl chloride (2.74 g, 13.8 mmol), 4-dimethylaminopyridine (1.10 g, 0.90 mmol) and triethylamine (3.20 mL, 23.0 mmol) in 100 mL of THF was stirred at 80° C. for 48 hours. The mixture was cooled to ambient temperature, diluted with 100 mL of ethyl acetate and washed with brine. The layers were separated and the aqueous phase was extracted with 2×50 mL ethyl acetate. The combined organic extracts were dried over anhydrous Na2SO4, filtered, and concentrated. Purification by column chromatography (SiO2, 20% ethyl acetate: 80% hexane) afforded 2.55 g of the title compound. 1H NMR (400 MHz, DMSO-d6) δ 1.67-1.72 (m, 6H) 1.92 (d, J=2.8 Hz, 6H) 1.97-2.04 (m, 3H) 7.55 (s, 1H) 11.50 (br m, 1H); MS (DCI/NH3) m/z 341 (M)+, 343 (M+2)+.

後処理

  1. temperatureThe mixture was cooled to ambient temperature
  2. washwashed with brine
  3. customThe layers were separated
  4. extractionthe aqueous phase was extracted with 2×50 mL ethyl acetate
  5. dry with materialThe combined organic extracts were dried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by column chromatography (SiO2, 20% ethyl acetate: 80% hexane)

出典と根拠

ORDレコード
ord-fbc07d08f3aa4060ba559cb17fc0b8cb
出典データセット
uspto-grants-2015_04
特許番号
US09006275B2

関連ノート

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