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 18333Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 18333
[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

Komponenten

7

Edukt 4

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

Produkt 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)-acrylamideAusbeute 47 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-cb2d1591d4c2443aae4db8bb276341db
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07741339B2

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