1,2-Dichloroethane → HCID 178481252, Verbindung

HRID 229989Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 229989
[C:1]([CH:5]1[CH2:10][CH2:9][CH:8]([N:11]([CH2:22][C:23]2[CH:31]=[CH:30][C:26]([C:27](O)=[O:28])=[CH:25][CH:24]=2)[C:12]2[N:16]([CH3:17])[C:15]3[CH:18]=[CH:19][CH:20]=[CH:21][C:14]=3[N:13]=2)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].O.[NH:33]1[C:37]([NH2:38])=[N:36][N:35]=[N:34]1.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.CCN(C(C)C)C(C)C>CN(C=O)C>[C:1]([CH:5]1[CH2:10][CH2:9][CH:8]([N:11]([CH2:22][C:23]2[CH:31]=[CH:30][C:26]([C:27]([NH:38][C:37]3[NH:36][N:35]=[N:34][N:33]=3)=[O:28])=[CH:25][CH:24]=2)[C:12]2[N:16]([CH3:17])[C:15]3[CH:18]=[CH:19][CH:20]=[CH:21][C:14]=3[N:13]=2)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2]

Komponenten

7

Edukt 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 688367154-{[(4-tert-Butylcyclohexyl)(1-methyl-1H-benzimidazol-2-yl)amino]methyl}-benzoic acidHCID 178509300HCID 178509300, Verbindung

Produkt 1

HCID 178481252HCID 178481252, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of the product of Example 5 Step A (0.14 mmol, 64 mg), 1H-tetraazol-5-amine monohydrate (0.28 mmol, 29 mg), HOBt (0.35 mmol, 53 mg) and EDC (0.56 mmol, 108 mg) in 1 mL of DMF was added DIEA (0.7 mmol, 122 μL). The reaction was allowed to stand at ambient temperature for 21 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 A). The product was lyophilized, affording a white solid. 1H NMR (500 MHz, CD3OD): δ 8.01 (d, 2H), 7.52-7.62 (overlapping m, 3H), 7.35-7.50 (overlapping m, 3H), 3.87 (s, 3H), 3.76 (m, 1H), 2.16 (m, 2H), 1.99 (m, 2H), 1.84 (m, 2H), 1.30 (m, 2H), 1.14 (m, 1H), 0.92 (s, 9H). MS (ESI): m/z 487 (M+H). HPLC A: 1.97 min.

Aufarbeitung

  1. concentrationconcentrated under reduced pressure
  2. custompurified by reverse-phase chromatography (Condition A)
  3. customaffording a white solid
  4. custom1.97 min.

Quellen und Nachweise

ORD-Eintrag
ord-4a942c6766c94bff86cb744fa3a7a2b1
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07563815B2

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