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

HRID 1470011Notes

Reaction equation

HRID 1470011 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

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)+.

Workup

  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)

Sources & evidence

ORD record
ord-2a0c58798f664b1689cb0be26780835c
Source dataset
uspto-grants-2015_04
Patent number
US09006275B2

Reaction notes

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