1,2-Dichloroethane → (E)-N-(7-chloro-1-methyl-1H-indol-3-ylmethyl)-N-methyl-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)-acrylamide

HRID 18333ノート

反応式

HRID 18333 の反応式
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[N:9]([CH3:11])[CH:8]=[C:7]2[CH2:12][NH:13][CH3:14].[O:15]=[C:16]1[NH:25][C:24]2[N:23]=[CH:22][C:21](/[CH:26]=[CH:27]/[C:28]([OH:30])=O)=[CH:20][C:19]=2[CH2:18][CH2:17]1.C1C=CC2N(O)N=NC=2C=1.O.C(Cl)CCl>CN(C=O)C.CCN(CC)CC>[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[N:9]([CH3:11])[CH:8]=[C:7]2[CH2:12][N:13]([CH3:14])[C:28](=[O:30])/[CH:27]=[CH:26]/[C:21]1[CH:22]=[N:23][C:24]2[NH:25][C:16](=[O:15])[CH2:17][CH2:18][C:19]=2[CH:20]=1

参加物

7

反応物 4

HCID 111,2-DichloroethaneHCID 27960291-Hydroxybenzotriazole hydrateHCID 11746081HCID 11746081、化合物HCID 221390677-Chloro-N,1-dimethyl-1H-indole-3-methanamine

生成物 1

HCID 10409212(E)-N-(7-chloro-1-methyl-1H-indol-3-ylmethyl)-N-methyl-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)-acrylamide収率 47%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8471Triethylamine溶媒

実験手順

A solution of 7-chloro-1-methyl-3-(methylaminomethyl)-1H-indole (104.3 mg, 0.5 mmole) and (E)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)-acrylic acid (109.1 mg, 0.5 mmole) in dry DMF (8 mL) was treated with dry Et3N (0.2 mL), HOBt H2O (76.5 mg, 0.5 mmole) and EDC (96 mg, 0.5 mmole). The solution was stirred at RT under argon for 20 h, then was concentrated. The oily residue was dissolved in MeOH and the solution was cooled. The precipitated solid was collected, washed with cold MeOH, and dried to give the title compound (95 mg, 47%): MS (ES) m/e 409.2 (M+H)+. Anal. Calcd for C22H21ClN4O2.0.25H2O: C, 63.92; H, 5.24; N, 13.55. Found: C, 63.56; H, 5.14; N, 13.73.

後処理

  1. concentrationwas concentrated
  2. dissolutionThe oily residue was dissolved in MeOH
  3. temperaturethe solution was cooled
  4. customThe precipitated solid was collected
  5. washwashed with cold MeOH
  6. customdried

出典と根拠

ORDレコード
ord-cb2d1591d4c2443aae4db8bb276341db
出典データセット
uspto-grants-2010_06
特許番号
US07741339B2

反応ノート

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