4-Methylmorpholine → Tert-butyl 2-(3-{[3-(2-methyl-1,3-dioxolan-2-yl)propanoyl]amino}quinolin-4-yl)hydrazinecarboxylate

HRID 415538Notes

Reaction equation

HRID 415538 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.[CH3:40][C:41]1([CH2:46][CH2:47][C:48](O)=[O:49])[O:45][CH2:44][CH2:43][O:42]1>CN(C)C1C=CN=CC=1.N1C=CC=CC=1.C(Cl)(Cl)Cl>[CH3:40][C:41]1([CH2:46][CH2:47][C:48]([NH:1][C:2]2[CH:3]=[N:4][C:5]3[C:10]([C:11]=2[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]=3)=[O:49])[O:45][CH2:44][CH2:43][O:42]1

Participants

8

Reactant 4

HCID 79724-MethylmorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 109317243-(2-methyl-1,3-dioxolan-2-yl)propanoic AcidHCID 21075823tert-butyl N'-(3-aminoquinolin-4-yl)hydrazinecarboxylate

Product 1

HCID 66620742Tert-butyl 2-(3-{[3-(2-methyl-1,3-dioxolan-2-yl)propanoyl]amino}quinolin-4-yl)hydrazinecarboxylateYield 100%

Reagents, catalysts & solvents 3

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

Conditions

Temperature
0 °C

Procedure

A mixture of tert-butyl N′-(3-aminoquinolin-4-yl)hydrazinecarboxylate (4.50 g, 16.4 mmol), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (3.93 g, 20.5 mmol), 4-methylmorpholine (2.29 mL, 20.5 mmol), and 4-dimethylaminopyridine (0.100 g, 0.82 mmol) in pyridine (120 mL) was chilled to 0° C. under an atmosphere of nitrogen. The mixture was treated drop-wise with a solution of 3-(2-methyl-[1,3]dioxolan-2-yl)-propionic acid (3.28 g, 20.5 mmol) in pyridine (30 mL). The reaction mixture was allowed to slowly come to ambient temperature. After 18 h, the reaction mixture was concentrated under reduced pressure to give a dark red oil. The oil was dissolved in chloroform (150 mL) and washed with 5% Na2CO3 aqueous solution (2×50 mL) and brine (50 mL), dried over Na2SO4, filtered, and concentrated under reduced pressure to yield 6.83 g of crude tert-butyl 2-(3-{[3-(2-methyl-1,3-dioxolan-2-yl)propanoyl]amino}quinolin-4-yl)hydrazinecarboxylate as a dark red oil.

Workup

  1. customto slowly come to ambient temperature
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. customto give a dark red oil
  4. washwashed with 5% Na2CO3 aqueous solution (2×50 mL) and brine (50 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-962d089524574729ab248f07265388a5
Source dataset
uspto-grants-2012_01
Patent number
US08088788B2

Reaction notes

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