Dimethyl Sulfoxide → 4-[3-Methyl-1-(7-methyl-quinoline-3-ylamino)-butyl]-benzoic acid ethyl ester

HRID 2281147노트

반응식

HRID 2281147 반응식
[NH2:1][CH:2]([C:6]1[CH:16]=[CH:15][C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:8][CH:7]=1)[CH2:3][CH2:4][CH3:5].Br[C:18]1[CH:19]=[N:20][C:21]2[C:26]([CH:27]=1)=[CH:25][CH:24]=[C:23]([CH3:28])[CH:22]=2.[CH3:29]S(C)=O>[Cu]I>[CH2:13]([O:12][C:10](=[O:11])[C:9]1[CH:15]=[CH:16][C:6]([CH:2]([NH:1][C:18]2[CH:19]=[N:20][C:21]3[C:26]([CH:27]=2)=[CH:25][CH:24]=[C:23]([CH3:28])[CH:22]=3)[CH2:3][CH:4]([CH3:29])[CH3:5])=[CH:7][CH:8]=1)[CH3:14]

참가 물질

5

반응물 3

HCID 679Dimethyl SulfoxideHCID 124656213-Bromo-7-methylquinolineHCID 71243833Ethyl(+/-)-4-(1-aminobutyl)benzoate

생성물 1

HCID 712393454-[3-Methyl-1-(7-methyl-quinoline-3-ylamino)-butyl]-benzoic acid ethyl ester수율 15%

시약·촉매·용매 1

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매

실험 절차

To a reaction vial with 4-(1-Amino-3-methyl-butyryl)-benzoic acid ethyl ester (2) (440 mg, 1.9 mM) was added DMSO (6.33 mL), 3-bromo-7-methylquinoline (9) (420 mg, 1.9 mM), followed by CuI catalyst (36 mg, 0.19 mM) and CsOAc (726 mg, 3.78 mM). The mixture was purged with argon gas and then the tube was sealed. The reaction mixture was heated to 100° for 48 h. The reaction mixture was cooled, diluted with EtOAc (10 mL), washed with water (3×5 mL), dried (Na2SO4) and concentrated. The crude material was separated by a 40 g silica gel with 0-80% EtOAc in heptane to give a yellow color product (108 mg, 15%). 1H NMR (500 MHz, CDCl3) δ ppm 0.98 (d, J=6.34 Hz, 3 H) 1.04 (d, J=6.34 Hz, 3 H) 1.39 (t, 3 H) 1.61-1.71 (m, 1 H) 1.71-1.86 (m, 2 H) 2.46 (s, 3 H) 4.36 (q, 2 H) 4.38-4.43 (m, 1 H) 4.47-4.56 (m, 1 H) 6.75 (d, J=1.95 Hz, 1 H) 7.20 (d, J=8.29 Hz, 1 H) 7.36 (d, J=8.05 Hz, 1 H) 7.47 (d, J=8.29 Hz, 2 H) 7.69 (s, 1 H) 8.03 (d, 2 H) 8.47 (br. s., 1 H). LC-MS: m/z 377.2 (M+1).

후처리

  1. customThe mixture was purged with argon gas
  2. customthe tube was sealed
  3. temperatureThe reaction mixture was heated to 100° for 48 h
  4. temperatureThe reaction mixture was cooled
  5. additiondiluted with EtOAc (10 mL)
  6. washwashed with water (3×5 mL)
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated
  9. customThe crude material was separated by a 40 g silica gel with 0-80% EtOAc in heptane

출처 및 근거

ORD 기록
ord-3ebbc65aa10c428fa6b27c977260e1c6
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09139538B2

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