三乙胺 → N-(5-bromo-1,3-thiazol-2-yl)adamantane-1-carboxamide

HRID 255075

反应方程式

HRID 255075 反应方程式
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

参与物

7

反应物 3

HCID 8471三乙胺HCID 98915金刚烷酰氯HCID 27238485-Bromothiazol-2-amine monohydrobromide

产物 1

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

试剂、催化剂与溶剂 3

HCID 142844-二甲氨基吡啶(DMAP)催化剂HCID 8028四氢呋喃溶剂HCID 8857乙酸乙酯溶剂

反应条件

温度
80 °C

实验过程

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 twice with 50 mL of 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, 6 H) 1.92 (d, J=2.8 Hz, 6 H) 1.97-2.04 (m, 3 H) 7.55 (s, 1 H) 11.50 (br m, 1 H); MS (DCI/NH3) m/z 341 (M)+, 343 (M+2)+.

后处理

  1. temperatureThe mixture was cooled to ambient temperature
  2. washwashed with brine
  3. customThe layers were separated
  4. extractionthe aqueous phase was extracted twice with 50 mL of 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)

来源与证据

ORD记录
ord-2906da847d944d67938b9b2a5c2bd97b
来源数据集
uspto-grants-2011_01
专利号
US07875639B2

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