1,2-Dichloroethane → (E)-N-methyl-N-(1-methyl-1H-indol-3-ylmethyl)-3-(8-oxo-6,7,8,9-tetrahydro-5H-pyrido[2,3-b]azepin-3-yl)acrylamide

HRID 1297462ノート

反応式

HRID 1297462 の反応式
C(Cl)CCl.Cl.[O:6]=[C:7]1[NH:13][C:12]2[N:14]=[CH:15][C:16](/[CH:18]=[CH:19]/[C:20]([OH:22])=O)=[CH:17][C:11]=2[CH2:10][CH2:9][CH2:8]1.[CH3:23][N:24]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:26]([CH2:33][NH:34][CH3:35])=[CH:25]1.C1C=CC2N(O)N=NC=2C=1.O.C(N(C(C)C)CC)(C)C>CN(C=O)C>[CH3:35][N:34]([CH2:33][C:26]1[C:27]2[C:32](=[CH:31][CH:30]=[CH:29][CH:28]=2)[N:24]([CH3:23])[CH:25]=1)[C:20](=[O:22])/[CH:19]=[CH:18]/[C:16]1[CH:15]=[N:14][C:12]2[NH:13][C:7](=[O:6])[CH2:8][CH2:9][CH2:10][C:11]=2[CH:17]=1

参加物

8

反応物 6

HCID 111,2-DichloroethaneHCID 962WaterHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 109867781-Methyl-3-(methylaminomethyl)indoleHCID 66905085(E)-3-(8-oxo-6,7,8,9-tetrahydro-5H-pyrido[2,3-b]azepin-3-yl)acrylic acid hydrochloride

生成物 1

HCID 22139148(E)-N-methyl-N-(1-methyl-1H-indol-3-ylmethyl)-3-(8-oxo-6,7,8,9-tetrahydro-5H-pyrido[2,3-b]azepin-3-yl)acrylamide収率 48%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

EDC (0.06 g, 0.30 mmole) was added to a solution of (E)-3-(8-oxo-6,7,8,9-tetrahydro-5H-pyrido[2,3-b]azepin-3-yl)acrylic acid hydrochloride salt (0.07 g, 0.27 mmole), 1-methyl-3-(methylaminomethyl)-1H-indole (0.05 g, 0.27 mmole), HOBt.H2O (0.04 g., 0.30 mmole) and diisopropylethylamine (0.14 mL, 0.81 mmole) in DMF (15 mL) at RT. The reaction was stirred overnight then was concentrated in vacuo. The residue was diluted with water and extracted with ethyl acetate. The combined organic extracts were washed with brine and dried over Na2SO4. Flash chromatography on silica gel (20% EtOH/EtOAc) gave title compound (0.05 g, 48%) as an off-white solid after drying in vacuo: MS (ES) m/e 389 (M+H)+.

後処理

  1. customat RT
  2. concentrationthen was concentrated in vacuo
  3. additionThe residue was diluted with water
  4. extractionextracted with ethyl acetate
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried over Na2SO4

出典と根拠

ORDレコード
ord-d083c54198cd4936b53d05f1eb45290d
出典データセット
uspto-grants-2007_07
特許番号
US07250424B2

反応ノート

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