1,2-Dichloroethane → HCID 178487300, Verbindung

HRID 230004Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 230004
[C:1]([CH:5]1[CH2:10][CH2:9][CH:8]([N:11]([CH2:24][C:25]2[CH:33]=[CH:32][C:28]([C:29]([OH:31])=O)=[CH:27][CH:26]=2)[C:12]2[N:16]([CH3:17])[C:15]3[CH:18]=[CH:19][C:20]([O:22][CH3:23])=[CH:21][C:14]=3[N:13]=2)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].O.[NH:35]1[C:39]([NH2:40])=[N:38][N:37]=[N:36]1.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.C(Cl)CCl>CN(C=O)C>[C:1]([CH:5]1[CH2:10][CH2:9][CH:8]([N:11]([CH2:24][C:25]2[CH:26]=[CH:27][C:28]([C:29]([NH:40][C:39]3[NH:38][N:37]=[N:36][N:35]=3)=[O:31])=[CH:32][CH:33]=2)[C:12]2[N:16]([CH3:17])[C:15]3[CH:18]=[CH:19][C:20]([O:22][CH3:23])=[CH:21][C:14]=3[N:13]=2)[CH2:7][CH2:6]1)([CH3:3])([CH3:2])[CH3:4]

Komponenten

7

Edukt 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 688349604-{[(4-Tert-butylcyclohexyl)(5-methoxy-1-methyl-1h-benzimidazol-2-yl)amino]methyl}benzoic acidHCID 178509300HCID 178509300, Verbindung

Produkt 1

HCID 178487300HCID 178487300, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

To a solution of the title compound of Example 14 Step D (0.1 mmol, 45 mg), 1H-tetraazol-5-amine monohydrate (0.2 mmol, 21 mg), HOBt (0.2 mmol, 31 mg) and DIEA (0.3 mmol, 52 μL) in 1 mL of DMF was added EDC (0.2 mmol, 38 mg). The reaction was heated to 40° C. for 3 h, then concentrated under reduced pressure. The residue was taken up in ca. 2:1 dioxane/H2O and acidified with TFA, then purified by reverse-phase chromatography (Condition B). The product was lyophilized affording a white solid. 1H NMR (500 MHz, d6-DMSO): δ 12.35 (s, 1H), 8.02 (d, 2H), 7.50-7.56 (overlapping m, 3H), 7.00 (d, 1H), 6.96 (m, 1H), 4.81 (s, 2H), 3.78 (s, 3H), 3.75 (s, 3H), 3.65 (m, 1H), 2.02 (m, 2H), 1.83 (m, 2H), 1.71 (m, 2H), 1.17 (m, 2H), 1.04 (m, 1H), 0.85 (s, 9H). MS (ESI): m/z 517 (M+H). HPLC A: 2.03 min.

Aufarbeitung

  1. concentrationconcentrated under reduced pressure
  2. custompurified by reverse-phase chromatography (Condition B)
  3. customThe product was lyophilized affording a white solid
  4. custom2.03 min.

Quellen und Nachweise

ORD-Eintrag
ord-e7b3915a6be748a8bbef9c5d0ddb8cbd
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07563815B2

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