Triethylamine → HCID 18128676, compound

HRID 1469988Notes

Reaction equation

HRID 1469988 reaction equation
Cl.[CH3:2][C:3]1[N:4]=[C:5]([NH2:9])[S:6][C:7]=1[CH3:8].C(N(CC)CC)C.[C:17]12([C:27](Cl)=[O:28])[CH2:26][CH:21]3[CH2:22][CH:23]([CH2:25][CH:19]([CH2:20]3)[CH2:18]1)[CH2:24]2>C1COCC1>[CH3:2][C:3]1[N:4]=[C:5]([NH:9][C:27]([C:17]23[CH2:26][CH:21]4[CH2:20][CH:19]([CH2:25][CH:23]([CH2:22]4)[CH2:24]2)[CH2:18]3)=[O:28])[S:6][C:7]=1[CH3:8]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 989151-Adamantanecarbonyl chlorideHCID 162113874,5-Dimethyl-1,3-thiazol-2-amine--hydrogen chloride (1/1)

Product 1

HCID 18128676HCID 18128676, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4,5-dimethyl-thiazol-2-ylamine hydrochloride (1.65 g, 10.0 mmol) in THF (100 mL) was added triethylamine (4.2 mL, 30 mmol) and adamantane-1-carbonyl chloride (2.2 g, 11 mmol). The mixture was heated at reflux overnight and then concentrated under reduced pressure. The residue was diluted with ethyl acetate, washed with 1M NaHCO3, dried (Na2SO4), filtered and concentrated. Purification by column chromatography (SiO2, 10% ethyl acetate: 90% hexanes) afforded 2.15 g (74%) of the title compound. MS (ESI+) m/z 291 (M+H)+.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux overnight
  3. concentrationconcentrated under reduced pressure
  4. additionThe residue was diluted with ethyl acetate
  5. washwashed with 1M NaHCO3
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification by column chromatography (SiO2, 10% ethyl acetate: 90% hexanes)

Sources & evidence

ORD record
ord-a1889fb69c2c461a8cf2c44f84ccafcb
Source dataset
uspto-grants-2015_04
Patent number
US09006275B2

Reaction notes

Loading…