1,2-Dichloroethane → HCID 59375005, Verbindung

HRID 1811105Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1811105
[C:1]([C:4]1[CH:5]=[CH:6][C:7]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[F:26])=[C:8]2[C:16]=1[NH:15][C:14]1[CH:13]=[C:12]([C:17](O)=[O:18])[CH:11]=[CH:10][C:9]2=1)(=[O:3])[NH2:2].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[CH3:50][N:51]1[CH2:56][CH2:55][CH:54]([NH2:57])[CH2:53][CH2:52]1>C1COCC1.CN(C=O)C>[F:26][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[C:7]1[C:8]2[C:9]3[C:14](=[CH:13][C:12]([C:17]([NH:57][CH:54]4[CH2:55][CH2:56][N:51]([CH3:50])[CH2:52][CH2:53]4)=[O:18])=[CH:11][CH:10]=3)[NH:15][C:16]=2[C:4]([C:1]([NH2:2])=[O:3])=[CH:5][CH:6]=1

Komponenten

8

Edukt 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27375314-Amino-1-methylpiperidineHCID 59375023HCID 59375023, Verbindung

Produkt 1

HCID 59375005HCID 59375005, VerbindungAusbeute 65,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of 8-carbamoyl-5-(2-fluorophenyl)-9H-carbazole-2-carboxylic acid (Example 23-2, 30 mg, 0.086 mmol), EDC (23.11 mg, 0.121 mmol), HOBT (18.46 mg, 0.121 mmol), DIEA (30 μL, 0.172 mmol), and 1-methylpiperidin-4-amine (9.83 mg, 0.086 mmol) in THF and DMF (4:1, 2 mL) was stirred at rt overnight. The mixture was concentrated and purified by preparative HPLC. The isolated product was partitioned between DCM and NaHCO3 (aq). The organic phase was dried and concentrated to provide 4-(2-fluorophenyl)-N7-(1-methylpiperidin-4-yl)-9H-carbazole-1,7-dicarboxamide as a white solid (25 mg, 62%). 1H NMR (400 MHz, DMSO-d6) δ 11.75 (s, 1 H) 8.24 (br. s., 1 H) 8.20 (s, 1 H) 8.13 (d, J=7.69 Hz, 1 H) 8.05 (d, J=7.91 Hz, 1 H) 7.52-7.68 (m, 3 H) 7.33-7.48 (m, 3 H) 7.13 (d, J=7.69 Hz, 1 H) 7.05 (d, J=8.35 Hz, 1 H) 3.64-3.80 (m, 1 H) 2.69-2.79 (m, 2 H) 1.87-2.00 (m, 2 H) 1.70-1.80 (m, 2 H) 1.48-1.65 (m, 2 H). Mass spectrum m/z 445.2 (M+H)+.

Aufarbeitung

  1. concentrationThe mixture was concentrated
  2. custompurified by preparative HPLC
  3. customThe isolated product was partitioned between DCM and NaHCO3 (aq)
  4. customThe organic phase was dried
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-0016ae49616d4448a3e23bc7e620c50f
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08362065B2

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