ホームMCPワークベンチSkills
ホームワークベンチ通知マイページ
llms.txt · MCPガイドプライバシーポリシー · 利用規約 · サポートv1.8.0
  1. ホーム
  2. /反応

1,2-Dichloroethane → Ethyl (+/-)-10,11-dihydro-3-[[[2-(2-pyridylamino)ethyl]amino]carbonyl]-5H-dibenzo[a,d]cycloheptene-10-acetate

HRID 613390
ノート
印刷プレビュー

反応式

HRID 613390 の反応式
C(Cl)CCl.[C:5]([C:8]1[CH:9]=[CH:10][C:11]2[CH2:17][CH:16]([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:15]3[CH:24]=[CH:25][CH:26]=[CH:27][C:14]=3[CH2:13][C:12]=2[CH:28]=1)(O)=[O:6].Cl.Cl.[NH2:31][CH2:32][CH2:33][NH:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][N:36]=1.C1C=CC2N(O)N=NC=2C=1.O.C(N(C(C)C)CC)(C)C>CN(C=O)C>[N:36]1[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=1[NH:34][CH2:33][CH2:32][NH:31][C:5]([C:8]1[CH:9]=[CH:10][C:11]2[CH2:17][CH:16]([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:15]3[CH:24]=[CH:25][CH:26]=[CH:27][C:14]=3[CH2:13][C:12]=2[CH:28]=1)=[O:6]
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 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 14238461N~1~-(Pyridin-2-yl)ethane-1,2-diamine--hydrogen chloride (1/2)HCID 15516628Ethyl (+/-)-10,11-dihydro-3-carboxy-5H-dibenzo[a,d]cycloheptene-10-acetate

生成物 1

HCID 54300392
Ethyl (+/-)-10,11-dihydro-3-[[[2-(2-pyridylamino)ethyl]amino]carbonyl]-5H-dibenzo[a,d]cycloheptene-10-acetate
収率 92%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

EDC (112.7 mg, 0.59 mmole) was added all at once to a solution of ethyl (±)-10,11-dihydro-3-carboxy-5H-dibenzo[a,d]cycloheptene-10-acetate (157.8 mg, 0.49 mmole), 2-[(2-aminoethyl)amino]pyridine dihydrochloride (123.5 mg, 0.59 mmole), HOBt.H2O (79.5 mg, 0.59 mmole), and diisopropylethylamine (0.43 mL, 2.45 mmole) in anhydrous DMF (2.5 mL) at RT. The reaction was stirred at RT for 18 hr, then was concentrated. The residue was reconcentrated from xylenes, then was diluted with H2O (5 mL) and extracted sequentially with EtOAc (2×5 mL) and CHCl3 (2×5 mL). The organic layers were combined and treated with a little MeOH to dissolve a small amount of insoluble material. Drying (MgSO4), concentration, and silica gel chromatography (5% MeOH/CHCl3) gave the title compound (199.1 mg, 92%) as a yellow oil: TLC (5% MeOH/CHCl3) Rf 0.42; 1H NMR (400, CDCl3) δ 8.10 (d, J=3.5 Hz, 1 H), 8.02 (br s, 1 H), 7.60 (app. narrow d, 1 H), 7.53 (app. dd, 1 H), 7.33-7.42 (m, 1 H), 7.08-7.22 (m, 5 H), 6.57-6.65 (m, 1 H), 6.45 (d, J=8.3 Hz, 1 H), 4.79-4.90 (m, 1 H), 4.36 (d,J=15.1 Hz, 1 H), 4.11-4.26 (m, 2 H), 3.92 (d, J=15.1 Hz, 1 H), 3.80-3.95 (m, 1 H), 3.55-3.72 (m, 4 H), 3.38 (dd, J=15.2, 4.1 Hz, 1 H), 3.03 (dd, J=15.2, 9.5 Hz, 1 H), 2.66 (dd, J=15.8,4.8 Hz, 1 H), 2.50 (dd, J=15.8, 9.6 Hz, 1 H), 1.27 (t, J=7.2 Hz, 3 H); MS (ES) m/e 444 (M+H)+.

後処理

  1. customat RT
  2. concentrationwas concentrated
  3. additionwas diluted with H2O (5 mL)
  4. extractionextracted sequentially with EtOAc (2×5 mL) and CHCl3 (2×5 mL)
  5. additiontreated with a little MeOH
  6. dissolutionto dissolve a small amount of insoluble material
  7. customDrying
  8. concentration(MgSO4), concentration, and silica gel chromatography (5% MeOH/CHCl3)

出典と根拠

ORDレコード
ord-d56b59534d314cb2b7c69255d7a3e17d
出典データセット
uspto-grants-1999_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06008213

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート