Diethylamine → N,N-Diethyl-4-{2-[(5-methyl-furan-2-ylmethyl)-amino]-quinolin-5-yl}-butyramide

HRID 1669723Notes

Reaction equation

HRID 1669723 reaction equation
[CH2:1]([NH:3][CH2:4][CH3:5])[CH3:2].C[Al](C)C.CO[C:12](=[O:34])[CH2:13][CH2:14][CH2:15][C:16]1[CH:25]=[CH:24][CH:23]=[C:22]2[C:17]=1[CH:18]=[CH:19][C:20]([NH:26][CH2:27][C:28]1[O:29][C:30]([CH3:33])=[CH:31][CH:32]=1)=[N:21]2>O1CCOCC1>[CH2:1]([N:3]([CH2:4][CH3:5])[C:12](=[O:34])[CH2:13][CH2:14][CH2:15][C:16]1[CH:25]=[CH:24][CH:23]=[C:22]2[C:17]=1[CH:18]=[CH:19][C:20]([NH:26][CH2:27][C:28]1[O:29][C:30]([CH3:33])=[CH:31][CH:32]=1)=[N:21]2)[CH3:2]

Participants

5

Reactant 3

HCID 8021DiethylamineHCID 16682925TrimethylaluminumHCID 442181534-{2-[(5-Methyl-furan-2-ylmethyl)-amino]-quinolin-5-yl}-butyric acid methyl ester

Product 1

HCID 44218155N,N-Diethyl-4-{2-[(5-methyl-furan-2-ylmethyl)-amino]-quinolin-5-yl}-butyramide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Diethylamine (89 mg, 1.22 mmol) was dissolved in 5 mL dioxane. Trimethylaluminium (2M solution in heptane, 0.61 mL, 1.22 mmol) was added and the mixture was stirred for 1 hour at room temperature. 4-{2-[(5-Methyl-furan-2-ylmethyl)-amino]-quinolin-5-yl}-butyric acid methyl ester (137 mg, 0.4 mmol) 7 mL dioxane was added and stirring was continued at 90° C. for 5 hours. The reaction mixture was quenched by addition of 0.6 mL water. The solvent was evaporated off. The residue was purified by flash chromatography on silica gel (heptane/ethyl acetate 100:0->0:100 gradient). The title compound was obtained as a yellow oil (40 mg, 26%), MS: m/e=380.5 (M+H+).

Workup

  1. stirringstirring
  2. waitwas continued at 90° C. for 5 hours
  3. customThe reaction mixture was quenched by addition of 0.6 mL water
  4. customThe solvent was evaporated off
  5. customThe residue was purified by flash chromatography on silica gel (heptane/ethyl acetate 100:0->0:100 gradient)

Sources & evidence

ORD record
ord-2afe320758af4a2d9c2192d861c3316b
Source dataset
uspto-grants-2011_08
Patent number
US07989628B2

Reaction notes

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