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

HRID 18334
ノート
印刷プレビュー

反応式

HRID 18334 の反応式
[CH2:1](Cl)[CH2:2]Cl.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:21])=[CH:17][C:11]=2[CH2:10][CH2:9][CH2:8]1.[CH3:23][C:24]1[NH:25][C:26]2[C:31]([C:32]=1[CH2:33][NH:34][CH3:35])=[CH:30][CH:29]=[CH:28][CH:27]=2.[CH:36]1C=CC2N(O)N=NC=2C=1.[OH2:46].C(N(C(C)C)CC)(C)C>CN(C=O)C>[CH3:36][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:31][CH2:32][CH2:24][CH2:23][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]/[CH:17]=[CH:16]/[CH2:18][CH:19]1[C:20](=[O:21])[O:22][C:2](=[O:46])[CH2:1]1.[CH3:35][N:34]([CH2:33][C:32]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[NH:25][C:24]=1[CH3:23])[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
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 5

HCID 111,2-DichloroethaneHCID 81531DiisopropylethylamineHCID 27960291-Hydroxybenzotriazole hydrateHCID 10954023N-Methyl-N-[(2-methyl-1H-indol-3-yl)methyl]amineHCID 66905085(E)-3-(8-oxo-6,7,8,9-tetrahydro-5H-pyrido[2,3-b]azepin-3-yl)acrylic acid hydrochloride

生成物 2

HCID 5363103
2,5-Furandione, dihydro-3-(2-octadecen-1-yl)-
HCID 10023175(E)-N-methyl-N-(2-methyl-1H-indol-3-yl methyl)-3-(8-oxo-6,7,8,9-tetrahydro-5H-pyrido[2,3-b]azepin-3-yl)acrylamide収率 76.9%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

EDC (0.18 g, 0.96 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 (0.24 g, 0.87 mmole), 2-methyl-3-(methylaminomethyl)indole (0.15 g, 0.87 mmole), HOBt H2O (0.13 g., 0.96 mmole) and diisopropylethylamine (0.45 mL, 2.61 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. Preparative HPLC on a Waters C-18 ODSA column (gradient: 20-100% H2O/CH3CN) gave the title compound (0.13 g, 38%) as a light yellow solid after drying in vacuo: MS (ES) m/e 389 (M+H)+.

後処理

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

出典と根拠

ORDレコード
ord-3a6af946cc7a4546a338c94184e70f94
出典データセット
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07741339B2

反応ノート

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