Diisopropylethylamine → HCID 11304839, Verbindung

HRID 2111235

Reaktionsgleichung

Reaktionsgleichung von HRID 2111235
[CH3:1][C@H:2]1[O:7][C@@H:6]([CH3:8])[CH2:5][NH:4][CH2:3]1.C(N(C(C)C)CC)(C)C.[CH:18]1([CH2:24][N:25]2[C:29]3[CH:30]=[CH:31][C:32]([C:34](O)=[O:35])=[CH:33][C:28]=3[N:27]=[C:26]2[C:37]([CH3:41])([CH3:40])[CH2:38][CH3:39])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.O>[CH:18]1([CH2:24][N:25]2[C:29]3[CH:30]=[CH:31][C:32]([C:34]([N:4]4[CH2:5][C@H:6]([CH3:8])[O:7][C@H:2]([CH3:1])[CH2:3]4)=[O:35])=[CH:33][C:28]=3[N:27]=[C:26]2[C:37]([CH3:40])([CH3:41])[CH2:38][CH3:39])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]1

Komponenten

7

Edukt 4

HCID 81531DiisopropylethylamineHCID 6415002,6-Dimethylmorpholine, cis-HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 576362581-(cyclohexylmethyl)-2-(1,1-dimethylpropyl)-1H-benzimidazole-5-carboxylic acid

Produkt 1

HCID 11304839HCID 11304839, VerbindungAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Following the same procedure in Example 3, Step A, using (2R,6S)-2,6-dimethylmorpholine (34.6 mg, 0.30 mmol), diisopropylethylamine (69.7 μL, 51.7 mg, 0.40 mmol) and a solution of 1-(cyclohexylmethyl)-2-(1,1-dimethylpropyl)-1H-benzimidazole-5-carboxylic acid (65.9 mg, 0.20 mmol) (for preparation, see in Example 4, Step E) in DMF (5 mL) at 0° C., and later, HATU (91.3 mg, 0.24 mmol). The mixture was stirred overnight at room temperature, added H2O (50 mL), extracted with EtOAc (3×50 mL). The desired title compound was purified by MPLC (hex/EtOAc 1:1 as eluent on silica gel) to give 75.7 mg (89%) of a white solid. 1H NMR (400 MHz, CD3OD): δ 0.86 (t, J=7.52 Hz, 3 H), 1.04 (m, 3 H), 1.28 (m, 8 H), 1.66 (m, 2 H), 1.69 (s, 6 H), 1.71 (m, 1 H), 1.79 (m, 2 H), 2.04 (q, J=7.42 Hz, 2 H), 2.13 (m, 1 H), 2.63 (m, 1 H), 2.92 (m, 1 H), 3.58 (m, 3 H), 4.50 (d, J=7.62 Hz, 2H), 4.55 (m, 1 H), 7.65 (dd, J=8.69, 1.46 Hz, 1 H), 7.81 (d, J=0.78 Hz, 1 H), 8.01 (d, J=8.79 Hz, 1 H). MS (ESI) (M+H)+=426.2. Anal. Calcd for C26H39N3O2+1.60 TFA+0.30 H2O (613.46): C, 57.17; H, 6.77; N, 6.85. Found: C, 57.18; H, 6.69; N, 6.88.

Aufarbeitung

  1. customat 0° C.
  2. extractionextracted with EtOAc (3×50 mL)
  3. customThe desired title compound was purified by MPLC (hex/EtOAc 1:1 as eluent on silica gel)

Quellen und Nachweise

ORD-Eintrag
ord-1d029be17fc84137a485fa383e6a21ac
Quelldatensatz
uspto-grants-2009_04
Patentnummer
US07517898B2

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