1,2-Dichloroethane → (E)-N-(2,3-dihydro-1H-3a-azacyclopenta[a]indene-8-ylmethyl)-N-methyl-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylamide

HRID 18327

Reaktionsgleichung

Reaktionsgleichung von HRID 18327
C(Cl)CCl.Cl.[O:6]=[C:7]1[NH:16][C:15]2[N:14]=[CH:13][C:12](/[CH:17]=[CH:18]/[C:19]([OH:21])=O)=[CH:11][C:10]=2[CH2:9][CH2:8]1.[CH3:22][NH:23][CH2:24][C:25]1[C:33]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[N:27]2[CH2:34][CH2:35][CH2:36][C:26]=12.C1C=CC2N(O)N=NC=2C=1.CCN(CC)CC>CN(C=O)C.O>[CH2:36]1[C:26]2=[C:25]([CH2:24][N:23]([CH3:22])[C:19](=[O:21])/[CH:18]=[CH:17]/[C:12]3[CH:13]=[N:14][C:15]4[NH:16][C:7](=[O:6])[CH2:8][CH2:9][C:10]=4[CH:11]=3)[C:33]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[N:27]2[CH2:34][CH2:35]1

Komponenten

8

Edukt 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 221390482,3-dihydro-8-(methylaminomethyl)-1H-3a-azacyclopenta[a]indeneHCID 66905305(E)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylic Acid Hydrochloride

Produkt 1

HCID 10092390(E)-N-(2,3-dihydro-1H-3a-azacyclopenta[a]indene-8-ylmethyl)-N-methyl-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylamideAusbeute 25 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

EDC (0.192 g, 1.0 mmole) was added to a solution of (E)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylic acid hydrochloride salt (0.254 g, 1.0 mmole), 2,3-dihydro-8-(methylaminomethyl)-1H-3a-azacyclopenta[a]indene (0.2 g, 1.0 mmole), HOBt. H2O (0.135 g, 1.0 mmole), and Et3N (0.15 mL, 1.1 mmole) in DMF (20 mL) at RT. The reaction was stirred overnight, then was poured into H2O (50 mL) and extracted with CH2Cl2 (2×30 mL). The combined extracts were washed with brine and dried (MgSO4). Flash chromatography on silica gel (5% MeOH/CH2Cl2) gave the title compound (0.1 g, 25%) a yellow solid: MS (ES) m/e 401 (M+H)+.

Aufarbeitung

  1. customat RT
  2. extractionextracted with CH2Cl2 (2×30 mL)
  3. washThe combined extracts were washed with brine
  4. dry with materialdried (MgSO4)

Quellen und Nachweise

ORD-Eintrag
ord-ed386be55d6b4488bd58e9a57fddd2c9
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07741339B2

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