1,2-Dichloroethane → HCID 67072439, Verbindung

HRID 2098461Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2098461
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([N:12]1[CH2:17][C@@H:16]2[CH2:18][C@H:13]1[CH2:14][N:15]2[C:19](=[O:26])[C@@H:20]([NH2:25])[C:21]([CH3:24])([CH3:23])[CH3:22])=[O:11].[CH3:27][C:28]1[CH:36]=[C:35]2[C:31]([CH:32]=[C:33]([C:37](O)=[O:38])[NH:34]2)=[CH:30][CH:29]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1>C(Cl)Cl.O>[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([N:12]1[CH2:17][C@@H:16]2[CH2:18][C@H:13]1[CH2:14][N:15]2[C:19]([C@@H:20]([NH:25][C:37]([C:33]1[NH:34][C:35]2[C:31]([CH:32]=1)=[CH:30][CH:29]=[C:28]([CH3:27])[CH:36]=2)=[O:38])[C:21]([CH3:22])([CH3:23])[CH3:24])=[O:26])=[O:11]

Komponenten

8

Edukt 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 31633966-Methyl-1H-indole-2-carboxylic acidHCID 58286598HCID 58286598, Verbindung

Produkt 1

HCID 67072439HCID 67072439, VerbindungAusbeute 60,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A solution of (2S)-1-[(1S,4S)-5-(1H-benzimidazol-2-ylcarbonyl)-2,5-diazabicyclo[2.2.1]hept-2-yl]-3,3-dimethyl-1-oxo-2-butanamine (120 mg, 0.34 mmol), 6-methyl-1H-indole-2-carboxylic acid (60 mg, 0.34 mmol), EDC (78 mg, 0.41 mmol), HOBt (9 mg, 0.068 mmol), NMM (103 mg, 1.02 mmol) in CH2Cl2 (2 mL) was stirred at room temperature for 18 h. The reaction was diluted with water and CH2Cl2 then washed with sat. NaHCO3 (20 mL) and brine (20 mL). The solution was dried over anhydrous Na2SO4 and concentrated to give the crude product, which was purified by reverse phase HPLC: 50-80% ACN/Water (0.1% TFA). Concentration of the fractions containing product afforded the title compound (105 mg) as a white solid. LCMS (m/z): 513.1 (M+H). 1H NMR (400 MHz, CDCl3) δ ppm: 0.90-1.10 (m, 9H), 1.75-2.20 (m, 2H), 2.30-2.40 (m, 3H), 3.45-3.95 (m, 3H), 4.00-5.25 m, 4H), 6.20-6.75 (m, 1H), 6.80-7.70 (m, 9H), 9.30-9.70 (m, 1H)

Aufarbeitung

  1. washthen washed with sat. NaHCO3 (20 mL) and brine (20 mL)
  2. dry with materialThe solution was dried over anhydrous Na2SO4
  3. concentrationconcentrated
  4. customto give the crude product, which
  5. customwas purified by reverse phase HPLC
  6. additionConcentration of the fractions containing product

Quellen und Nachweise

ORD-Eintrag
ord-902f6497c96a446c9569eb7924b69e51
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08450484B2

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