Diisopropylethylamine → HCID 11234462, Verbindung

HRID 2111236

Reaktionsgleichung

Reaktionsgleichung von HRID 2111236
Cl.[O:2]1[CH2:6][CH2:5][CH2:4][NH:3]1.C(N(C(C)C)CC)(C)C.[CH:16]1([CH2:22][N:23]2[C:27]3[CH:28]=[CH:29][C:30]([C:32](O)=[O:33])=[CH:31][C:26]=3[N:25]=[C:24]2[C:35]([CH3:39])([CH3:38])[CH2:36][CH3:37])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[CH:16]1([CH2:22][N:23]2[C:27]3[CH:28]=[CH:29][C:30]([C:32]([N:3]4[CH2:4][CH2:5][CH2:6][O:2]4)=[O:33])=[CH:31][C:26]=3[N:25]=[C:24]2[C:35]([CH3:38])([CH3:39])[CH2:36][CH3:37])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]1

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 12304500Isoxazolidine hydrochlorideHCID 576362581-(cyclohexylmethyl)-2-(1,1-dimethylpropyl)-1H-benzimidazole-5-carboxylic acid

Produkt 1

HCID 11234462HCID 11234462, VerbindungAusbeute 98,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Following the same procedure in Example 3, Step A, using isoxazolidine hydrochoride (29.5 mg, 0.26 mmol), diisopropylethylamine (144 μL, 106.6 mg, 0.83 mmol) and a solution of 1-(cyclohexylmethyl)-2-(1,1-dimethylpropyl)-1H-benzimidazole-5-carboxylic acid (82.1 mg, 0.25 mmol) (for preparation, see in Example 4, Step E) in DMF (5 mL) at 0° C., and later, HATU (114.0 mg, 0.30 mmol). The mixture was stirred for 4 h at room temperature, and quenched by adding H2O (5 mL). Upon evapoartion, the desired title compound was purified by reversed-phase HPLC (C-18 column) using 20-50% CH3CN/H2O to give 94.8 mg (76%) of a white solid. 1H NMR (400 MHz, CD3OD): δ 0.86 (t, J=7.42 Hz, 3 H), 1.27 (m, 5 H), 1.66 (m, 3 H), 1.69 (s, 6 H), 1.79 (m, 2 H), 2.04 (q, J=7.49 Hz, 2 H), 2.13 (m, 1 H), 2.43 (m, 2 H), 3.94 (m, 2 H), 4.07 (t, J=6.74 Hz, 2 H), 4.50 (d, J=7.62 Hz, 2 H), 8.00 (m, 2 H), 8.19 (s, 1 H). MS (ESI) (M+H)+=384.2. Anal. Calcd for C23H33N3O2+1.40 TFA+1.30 H2O (566.59): C, 54.69; H, 6.58; N, 7.42. Found: C, 54.66; H, 6.50; N, 7.68.

Aufarbeitung

  1. customat 0° C.
  2. customquenched
  3. additionby adding H2O (5 mL)
  4. customUpon evapoartion, the desired title compound was purified by reversed-phase HPLC (C-18 column)

Quellen und Nachweise

ORD-Eintrag
ord-c93d3ff9175148ec9ab4b3e9a1f3add1
Quelldatensatz
uspto-grants-2009_04
Patentnummer
US07517898B2

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