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1,2-Dichloroethane → (E)-3-(6-aminopyridin-3-yl)-2-methyl-N-methyl-N-(1-methyl-1H-indol-2-ylmethyl)acrylamide

HRID 225933
ノート
印刷プレビュー

反応式

HRID 225933 の反応式
Cl.[NH2:2][C:3]1[N:8]=[CH:7][C:6](/[CH:9]=[C:10](\[CH3:14])/[C:11]([OH:13])=O)=[CH:5][CH:4]=1.[CH3:15][N:16]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[C:17]1[CH2:25][NH:26][CH3:27].C1C=CC2N(O)N=NC=2C=1.O.CCN(CC)CC.C(Cl)CCl>CN(C=O)C.C(Cl)Cl>[NH2:2][C:3]1[N:8]=[CH:7][C:6](/[CH:9]=[C:10](\[CH3:14])/[C:11]([N:26]([CH3:27])[CH2:25][C:17]2[N:16]([CH3:15])[C:24]3[C:19]([CH:18]=2)=[CH:20][CH:21]=[CH:22][CH:23]=3)=[O:13])=[CH:5][CH:4]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 6

HCID 111,2-DichloroethaneHCID 962WaterHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 11401058methyl((1-methyl-1H-indol-2-yl)methyl)amineHCID 67343937(E)-3-(6-aminopyridin-3-yl)2-methylacrylic acid HCl salt

生成物 1

HCID 57440853
(E)-3-(6-aminopyridin-3-yl)-2-methyl-N-methyl-N-(1-methyl-1H-indol-2-ylmethyl)acrylamide
収率 75%

試薬・触媒・溶媒 1

HCID 22350042dichloromethane N,N-dimethylformamide溶媒

実験手順

To a stirred solution of (E)-3-(6-aminopyridin-3-yl)-2-methylacrylic acid HCl salt (0.5 g, 2.3 mmole) in dry 1:1 DMF/CH2Cl2 (30 mL) at RT was added 1-methyl-2-(methylaminomethyl)indole (0.42 g, 2.4 mmole), HOBt.H2O (0.32 g, 2.4 mmole), Et3N (0.66 mL, 4.7 mmole), and EDC (0.46 g, 2.4 mmole). After stirring for 24 hr the reaction was concentrated to dryness. The residue was taken up in ethyl acetate and the solution was washed with H2O, dried (Na2SO4), and concentrated under vacuum. Flash chromatography on silica gel (4% methanol/CHCl3) followed by trituaation with ethyl acetate/hexane gave the title compound (0.55 g, 75%) as an off-white solid: LCMS (ES) m/e 335.2 (M+H)+; 1H NMR (300 MHz, DMSO-d6) δ 7.96 (s, 1 H), 7.52 (d, J=7.8 Hz, 1 H), 7.48 (dd, 1 H), 7.43 (d, J=7.8 Hz, 1 H), 7.14 (t, 1 H), 7.03 (t, 1 H), 6.46 (d, J=8.7 Hz, 1 H), 6.43 (s, 1 H), 6.40 (s, 1 H), 6.17 (br s, 2 H).

後処理

  1. concentrationwas concentrated to dryness
  2. washthe solution was washed with H2O
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated under vacuum

出典と根拠

ORDレコード
ord-10cc9a1e63994cb89c0e33962e40d157
出典データセット
uspto-grants-2009_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07557125B2

反応ノート

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