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1,2-Dichloroethane → (E)-3-[6-aminopyridin-3-yl]-N-methyl-N-(3-methyl-4H-inden-2-ylmethyl)acrylamide

HRID 2112704
ノート
印刷プレビュー

反応式

HRID 2112704 の反応式
C(Cl)CCl.[NH2:5][C:6]1[N:11]=[CH:10][C:9](/[CH:12]=[CH:13]/[C:14]([OH:16])=O)=[CH:8][CH:7]=1.Cl.[CH3:18][C:19]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH2:21][C:20]=1[CH2:28][NH:29][CH3:30].C1C=CC2N(O)N=NC=2C=1.O.C(N(CC)CC)C>CN(C=O)C>[NH2:5][C:6]1[N:11]=[CH:10][C:9](/[CH:12]=[CH:13]/[C:14]([N:29]([CH3:30])[CH2:28][C:20]2[C:19]([CH3:18])=[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH2:26]3)[CH:21]=2)=[O:16])=[CH:8][CH:7]=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 10487224(2E)-3-(6-aminopyridin-3-yl)prop-2-enoic acidHCID 221382193-Methyl-2-(methylaminomethyl)indene hydrochloride

生成物 1

HCID 57440847
(E)-3-[6-aminopyridin-3-yl]-N-methyl-N-(3-methyl-4H-inden-2-ylmethyl)acrylamide
収率 52%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

EDC (0.383 g, 2.0 mmole) was added to a solution of (E)-3-(6-aminopyridin-3-yl)acrylic acid (0.328 g, 2.0 mmole), 3-methyl-2-(methylaminomethyl)indene hydrochloride (0.420 g, 2.0 mmole), HOBt.H2O (0.306 g, 2.0 mmole), and triethylamine (0.57 mL, 4.0 mmole) in anhydrous DMF (18 mL) at RT. The reaction was stirred overnight and concentrated in vacuo. The residue was diluted with 5% NaHCO3 and extracted with CH2Cl2. The combined organic extracts were washed with brine and dried over MgSO4. Flash chromatography on silica gel (3% MeOH/CH2Cl2) gave the title compound (0.33 g, 52%) as a colorless solid: MS (ES) m/e 320.2 (M+H)+. Anal. Calcd for C20H21N3O.0.4H2O: C, 73.57; H, 6.72; N, 12.86. Found: C, 73.94; H, 6.92; N, 12.50.

後処理

  1. customat RT
  2. concentrationconcentrated in vacuo
  3. additionThe residue was diluted with 5% NaHCO3
  4. extractionextracted with CH2Cl2
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried over MgSO4

出典と根拠

ORDレコード
ord-e49c1fe45e364d1f9ff39b85ee9e1152
出典データセット
uspto-grants-2009_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07524843B2

反応ノート

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