4-Methylmorpholine → tert-butyl N'-[3-(3,3-diethoxypropionylamino)quinolin-4-yl]hydrazinecarboxylate

HRID 415543Notes

Reaction equation

HRID 415543 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[NH:12][NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[CH:9][CH:8]=[CH:7][CH:6]=2.Cl.CN(C)CCCN=C=NCC.CN1CCOCC1.[CH2:40]([O:42][CH:43]([O:48][CH2:49][CH3:50])[CH2:44][C:45](O)=[O:46])[CH3:41]>CN(C)C1C=CN=CC=1.N1C=CC=CC=1.C(Cl)(Cl)Cl>[CH2:40]([O:42][CH:43]([O:48][CH2:49][CH3:50])[CH2:44][C:45]([NH:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[NH:12][NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[CH:9][CH:8]=[CH:7][CH:6]=2)=[O:46])[CH3:41]

Participants

8

Reactant 4

HCID 79724-MethylmorpholineHCID 4152823,3-Diethoxypropanoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 21075823tert-butyl N'-(3-aminoquinolin-4-yl)hydrazinecarboxylate

Product 1

HCID 66619949tert-butyl N'-[3-(3,3-diethoxypropionylamino)quinolin-4-yl]hydrazinecarboxylateYield 99.9%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent2×HCID 6212ChloroformSolvent

Procedure

A mixture of tert-butyl N′-(3-aminoquinolin-4-yl)hydrazinecarboxylate (9.01 g, 32.9 mmol), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (7.56 g, 39.4 mmol), 4-methylmorpholine (4.34 mL, 39.4 mmol), and 4-dimethylaminopyridine (0.200 g, 1.64 mmol) in pyridine (200 mL) was chilled in an ice-water under a nitrogen atmosphere. The mixture was treated drop-wise with a solution of 3,3-diethoxypropionic acid (6.40 g, 39.4 mmol) in pyridine (50 mL). The reaction was allowed to slowly come to ambient temperature and stirred overnight. After 15 h, the reaction mixture was concentrated under reduced pressure to yield a dark red solid. The solid was dissolved in chloroform (150 mL) and transferred to a separatory funnel. The organic solution was washed with 10% Na2CO3 aqueous solution (35 mL), water (2×35 mL), and brine (35 mL), dried over Na2SO4, filtered, and concentrated under reduced pressure to yield 13.75 g of crude tert-butyl N′-[3-(3,3-diethoxypropionylamino)quinolin-4-yl]hydrazinecarboxylate as a dark red solid.

Workup

  1. customto slowly come to ambient temperature
  2. waitAfter 15 h
  3. concentrationthe reaction mixture was concentrated under reduced pressure
  4. customto yield a dark red solid
  5. customtransferred to a separatory funnel
  6. washThe organic solution was washed with 10% Na2CO3 aqueous solution (35 mL), water (2×35 mL), and brine (35 mL)
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f0375f165f7842e6a3862e5fa6ccb4ff
Source dataset
uspto-grants-2012_01
Patent number
US08088788B2

Reaction notes

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