Triethylamine → HCID 86718989, compound

HRID 1746268Notes

Reaction equation

HRID 1746268 reaction equation
[CH2:1]([O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][O:10][C:11]1[CH:17]=[CH:16][C:14]([NH2:15])=[CH:13][CH:12]=1)[C:2]#[CH:3].Cl[C:19]([O:21][C:22]1[CH:27]=CC([N+]([O-])=O)=CC=1)=[O:20].C(N(CC)CC)C.[C:38](OCC)(=[O:41])[NH:39][NH2:40].C(=O)(O)[O-].[Na+]>C1COCC1>[CH2:1]([O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][O:10][C:11]1[CH:17]=[CH:16][C:14]([NH:15][C:38]([NH:39][NH:40][C:19]([O:21][CH2:22][CH3:27])=[O:20])=[O:41])=[CH:13][CH:12]=1)[C:2]#[CH:3]

Participants

7

Reactant 5

HCID 8471Triethylamine2×HCID 20064Hydrazinecarboxylic acid, ethyl esterHCID 821294-Nitrophenyl chloroformateHCID 516892Sodium BicarbonateHCID 86718988HCID 86718988, compound

Product 1

HCID 86718989HCID 86718989, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 4-(2-(2-(prop-2-ynyloxy)ethoxy)ethoxy)aniline (I-7b: 1.339 g, 5.69 mmol) in THF (37.9 mL) at 0° C. was added 4-nitrophenyl chloroformate (2.064 g, 10.24 mmol) and triethylamine (1.420 mL, 10.24 mmol). The mixture was stirred at room temperature for 1 hour. Then ethyl carbazate (1.540 g, 14.79 mmol) and more triethylamine (1.420 mL, 10.24 mmol) were added. The mixture was stirred at room temperature for 16 hours, followed by the addition of aqueous saturated sodium bicarbonate. The mixture was then extracted twice with ethyl acetate, dried over MgSO4, filtered, and then concentrated in vacuo. The crude product was purified by silica gel chromatography (40-100% ethyl acetate/heptane) giving ethyl 2-(4-(2-(2-(prop-2-ynyloxy)ethoxy)ethoxy)phenylcarbamoyl)-hydrazinecarboxylate (I-7c: 1.31 g, 63%) as a foamy colorless oil. LC-MS (M+1) 366.1, t=0.95 minute.

Workup

  1. stirringThe mixture was stirred at room temperature for 16 hours
  2. extractionThe mixture was then extracted twice with ethyl acetate
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by silica gel chromatography (40-100% ethyl acetate/heptane)

Sources & evidence

ORD record
ord-8b6ae8d09a6a427097761cc3ee3b48d9
Source dataset
uspto-grants-2015_10
Patent number
US09149541B2

Reaction notes

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