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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 1362143
ノート
印刷プレビュー

反応式

HRID 1362143 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

9

反応物 6

HCID 111,2-DichloroethaneHCID 962WaterHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 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 38%

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. 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-4b260c70b9b449f4895e2862d1406c03
出典データセット
uspto-grants-2011_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07879872B2

反応ノート

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