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

HRID 1424276ノート

反応式

HRID 1424276 の反応式
[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>>[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]

参加物

4

反応物 3

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

生成物 1

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

実験手順

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 Cul 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, 3H) 1.04 (d, J=6.34 Hz, 3H) 1.39 (t, 3H) 1.61-1.71 (m, 1H) 1.71-1.86 (m, 2H) 2.46 (s, 3H) 4.36 (q, 2H) 4.38-4.43 (m, 1H) 4.47-4.56 (m, 1H) 6.75 (d, J=1.95 Hz, 1H) 7.20 (d, J=8.29 Hz, 1H) 7.36 (d, J=8.05 Hz, 1H) 7.47 (d, J=8.29 Hz, 2H) 7.69 (s, 1H) 8.03 (d, 2H) 8.47 (br. s., 1H). LC-MS: m/z 377.2 (M+1).

後処理

  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

出典と根拠

ORDレコード
ord-674a1149871d4fd1a2ad687bb3c3fc94
出典データセット
uspto-grants-2015_01
特許番号
US08927577B2

反応ノート

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