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

HRID 1669723노트

반응식

HRID 1669723 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

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+).

후처리

  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)

출처 및 근거

ORD 기록
ord-2afe320758af4a2d9c2192d861c3316b
출처 데이터셋
uspto-grants-2011_08
특허 번호
US07989628B2

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