Triethylamine → HCID 67499154, compound

HRID 1502579Notes

Reaction equation

HRID 1502579 reaction equation
Cl.[C:2](=[NH:7])(OCC)[CH3:3].C(N(CC)CC)C.[NH:15]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[NH2:16].Br.Br[CH2:26][C:27]([C:29]1[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=1)=O>C(O)C>[CH3:3][C:2]1[N:16]([NH:15][C:17](=[O:18])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH:26]=[C:27]([C:29]2[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=2)[N:7]=1

Participants

6

Reactant 4

HCID 8471Triethylamine2×HCID 70091tert-Butyl carbazateHCID 2724290Ethanimidic acid, ethyl ester, hydrochloride (1:1)HCID 27762343-(2-Bromoacetyl)pyridine hydrobromide

Product 1

HCID 67499154HCID 67499154, compoundYield 17.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent3×

Procedure

To a mixture of ethyl acetimidate hydrochloride (2.0 g, 16.20 mmol) and triethylamine (3.28 g, 32.4 mmol) in ethanol (40 mL) was added a solution of tert-butyl hydrazinecarboxylate (2.14 g, 16.20 mmol) in ethanol (10 mL) at room temperature. The resulting mixture was stirred at room temperature overnight. Then to the mixture was added a solution of 2-bromo-1-(pyridin-3-yl)ethanone hydrobromide (5.0 g, 17.9 mmol) and triethylamine (4.9 g, 48.6 mmol) in ethanol (20 mL). The reaction mixture was stirred at room temperature for 5 hours then heated to reflux overnight. The solvent was removed under reduced pressure and the residue was purified via silica gel chromatography (dichloromethane: methanol, 10:1) to give the title compound as an orange oil (0.76 g, 17.3%): 1H NMR (300 MHz, CDCl3) δ 8.87 (s, 1H), 8.45 (d, 1H, J=6.3 Hz), 8.43 (s, 1H), 8.05 (d, 1H, J=6.3 Hz), 7.33-7.25 (m, 2H), 2.37 (s, 3H), 1.51 (s, 9H); ESIMS m/z 275 [(M+H)]+.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 5 hours
  2. temperaturethen heated
  3. temperatureto reflux overnight
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified via silica gel chromatography (dichloromethane: methanol, 10:1)

Sources & evidence

ORD record
ord-9c2452a6ab334bab92255a505c3a743b
Source dataset
uspto-grants-2015_12
Patent number
US09210931B2

Reaction notes

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