Triethylamine → Ammonium Acetate

HRID 255056

Reaktionsgleichung

Reaktionsgleichung von HRID 255056
[F:1][C:2]1[CH:18]=[CH:17][C:5]([CH2:6][C:7]2[S:11][C:10](=[NH:12])[N:9]([CH2:13][CH2:14][O:15][CH3:16])[CH:8]=2)=[CH:4][CH:3]=1.[CH2:19]1[CH:26]2[C:22]3([C:28]([OH:30])=[O:29])[CH2:23][CH:24]([CH2:27][CH:20]1[CH2:21]3)[CH2:25]2.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C>CN(C=O)C.C(OCC)(=O)C>[C:28]([O-:30])(=[O:29])[CH3:22].[NH4+:9].[F:1][C:2]1[CH:18]=[CH:17][C:5]([CH2:6][C:7]2[S:11][C:10](=[N:12][C:28]([C:22]34[CH2:23][CH:24]5[CH2:27][CH:20]([CH2:19][CH:26]3[CH2:25]5)[CH2:21]4)=[O:29])[N:9]([CH2:13][CH2:14][O:15][CH3:16])[CH:8]=2)=[CH:4][CH:3]=1

Komponenten

8

Edukt 4

HCID 8471TriethylamineHCID 2733865Hexahydro-2,5-methanopentalene-3a(1H)-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 668590705-(4-fluoro-benzyl)-3-(2-methoxyethyl)-3H-thiazol-2-ylidene-amine

Produkt 2

HCID 517165Ammonium AcetateHCID 24890079HCID 24890079, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of the product of Example 43A (342 mg, 1.29 mmol), hexahydro-2,5-methano-pentalene-3a-carboxylic acid (256 mg, 1.54 mmol), HATU (737 mg, 1.24 mmol) and triethylamine (1.08 mL, 7.74 mmol) in 20 mL of DMF was stirred at room temperature for overnight. The mixture was diluted with ethyl acetate and washed with water. The organic extract was dried (MgSO4), filtered and concentrated. The residue was purified by preparative HPLC on a Waters Symmetry C8 column (40 mm×100 mm, 7 μm particle size) using a gradient of 10% to 100% acetonitrile:ammonium acetate (10 mM) over 15 minutes at a flow rate of 70 mL/minutes to afford the title compound: 1H NMR (500 MHz, DMSO-d6l) δ 1.51-1.61 (m, 4 H) 1.64-1.75 (m, 4 H) 2.06 (d, J=9.2 Hz, 2 H) 2.22-2.27 (m, 2 H) 2.51-253 (m, 1 H) 3.25 (s, 3 H) 3.67 (t, J=5.3 Hz, 2 H) 3.95 (s, 2 H) 4.23 (t, J=5.2 Hz, 2 H) 7.15 (t, J=8.8 Hz, 2 H) 7.23 (s, 1 H) 7.29 (dd, J=8.4, 5.6 Hz, 2 H); MS (DCI/NH3) m/z 415 (M+H)+.

Aufarbeitung

  1. washwashed with water
  2. extractionThe organic extract
  3. dry with materialwas dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by preparative HPLC on a Waters Symmetry C8 column (40 mm×100 mm, 7 μm particle size)

Quellen und Nachweise

ORD-Eintrag
ord-b41986b26a734960a50032a3735f249e
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07875639B2

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