Diisopropylethylamine → HCID 178499392, compound

HRID 2301971Notes

Reaction equation

HRID 2301971 reaction equation
FC(F)(F)C(O)=O.[CH3:8][O:9][C:10](=[O:27])[CH2:11][CH:12]1[CH2:21][C:20]2[C:15](=[CH:16][C:17]([O:22][CH2:23][CH2:24][NH2:25])=[CH:18][CH:19]=2)[NH:14][C:13]1=[O:26].[N+]([O-])(O)=O.CC1([C:39]([NH2:41])=[NH:40])C=C(C)N=N1.C(N(C(C)C)CC)(C)C>O1CCOCC1.O>[CH3:8][O:9][C:10](=[O:27])[CH2:11][CH:12]1[CH2:21][C:20]2[C:15](=[CH:16][C:17]([O:22][CH2:23][CH2:24][NH:25][C:39]([NH2:41])=[NH:40])=[CH:18][CH:19]=2)[NH:14][C:13]1=[O:26]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 694865753,5-Dimethylpyrazole carboxamidine nitrateHCID 69979259[7-(2-Amino-ethoxy)-2-oxo-1,2,3,4-tetrahydro-quinolin-3-yl]-acetic Acid Methyl Ester Trifluoroacetate

Product 1

HCID 178499392HCID 178499392, compoundYield 85.4%

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

A suspension of [7-(2-amino-ethoxy)-2-oxo-1,2,3,4-tetrahydro-quinolin-3-yl]-acetic acid methyl ester trifluoroacetate (1.49 g, 3.8 mmol), 3,5-dimethylpyrazole carboxamidine nitrate (0.84 g, 4.18 mmol) and diisopropylethylamine (1.45 mL, 8.32 mmol) in 3:1 dioxane-water (11 mL) were heated at reflux for 22 h. The cooled solution was concentrated in vacuo to yield a viscous yellow syrup. Washing the syrup with ice-cold water (3×5 ml) gives the title compound as a dried white solid (1.04 g).

Workup

  1. temperaturewere heated
  2. temperatureat reflux for 22 h
  3. concentrationThe cooled solution was concentrated in vacuo
  4. customto yield a viscous yellow syrup
  5. washWashing the syrup with ice-cold water (3×5 ml)

Sources & evidence

ORD record
ord-c282c54c4d8948019e074d8c8b9797c2
Source dataset
uspto-grants-2002_08
Patent number
US06429214B1

Reaction notes

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