Diisopropylethylamine → HCID 11395852, Verbindung

HRID 2111237

Reaktionsgleichung

Reaktionsgleichung von HRID 2111237
Cl.[CH3:2][C@:3]1([OH:8])[CH2:7][O:6][NH:5][CH2:4]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:5]4[CH2:4][C@@:3]([CH3:2])([OH:8])[CH2:7][O:6]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 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 acidHCID 68962815HCID 68962815, Verbindung

Produkt 1

HCID 11395852HCID 11395852, VerbindungAusbeute 87,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Following the same procedure in Example 3, Step A, using (4R)-4-methylisoxazolidin-4-ol hydrochoride (36.0 mg, 0.25 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 ( 14.0 mg, 0.30 mmol). The mixture was stirred for 4 h at room temperature, added 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 90.5 mg (69%) of a white solid. [a]D: +16.6° (c 0.15,EtOH). 1H NMR (400 MHz, CD3OD): δ 0.86 (t, J=7.42 Hz, 3H), 1.26 (m, 5H), 1.50 (s, 3H), 1.66 (m, 3H), 1.69 (s, 6H), 1.79 (m, 2H), 2.04 (q, J=7.49 Hz, 2H), 2.13 (m, 1H), 3.82 (d, J=11.33 Hz, 1H), 3.89 (d, J=8.40 Hz, 1H), 3.97 (m, 2H), 4.50 (d, J=7.81 Hz, 2H), 7.99 (m,2H), 8.19 (s, 1H). MS (ESI) (M+H)+=414.2. Anal. Calcd for C24H35N3O3+1.50 TFA+1.10 H2O (604.42): C, 53.65; H, 6.45; N, 6.95. Found: C, 53.55; H, 6.44; N, 7.18.

Aufarbeitung

  1. customat 0° C.
  2. customUpon evapoartion, the desired title compound was purified by reversed-phase HPLC (C-18 column)

Quellen und Nachweise

ORD-Eintrag
ord-551b06f5230949039dcffc108d258935
Quelldatensatz
uspto-grants-2009_04
Patentnummer
US07517898B2

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