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

HRID 1669723ノート

反応式

HRID 1669723 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

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+).

後処理

  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)

出典と根拠

ORDレコード
ord-2afe320758af4a2d9c2192d861c3316b
出典データセット
uspto-grants-2011_08
特許番号
US07989628B2

反応ノート

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