Triethylamine → HCID 178426909, Verbindung

HRID 56346

Reaktionsgleichung

Reaktionsgleichung von HRID 56346
Cl.Cl.[F:3][C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:18])[CH2:11][N:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)=[CH:6][CH:5]=1.[CH3:19][C:20]1[CH:24]=[C:23]([C:25](O)=[O:26])[NH:22][N:21]=1.C(N(CC)CC)C>CN(C=O)C>[F:3][C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:18])[CH2:11][N:12]2[CH2:13][CH2:14][N:15]([C:25]([C:23]3[NH:22][N:21]=[C:20]([CH3:19])[CH:24]=3)=[O:26])[CH2:16][CH2:17]2)=[CH:6][CH:5]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 429337161-(4-Fluorophenyl)-2-(piperazin-1-yl)ethan-1-one dihydrochlorideHCID 178427254HCID 178427254, Verbindung

Produkt 1

HCID 178426909HCID 178426909, VerbindungAusbeute 78,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 1-(4-fluorophenyl)-2-(piperazin-1-yl)ethanone dihydrochloride (29.5 mg, 0.100 mmol, from Step B of Example 1.1), 3-methyl-1H-pyrazole-5-carboxylic acid (18.9 mg, 0.150 mmol), and triethylamine (0.139 mL, 1.00 mmol) in DMF (0.5 mL) was added 1-propylphosphonic acid anhydride solution (50 wt. % in ethyl acetate, 122 μL, 0.200 mmol). The mixture was stirred for 2 h, quenched with water and purified by preparative HPLC/MS. The resultant lyophilate was dissolved in DCM, treated with MP-carbonate resin (˜100 mg). The mixture was stirred for 30 min and filtered to remove the resin. The solvent was removed under reduce pressure to afford the title compound (26.0 mg) as a white solid. 1H NMR (400 MHz, CDCl3) δ 2.34 (s, 3H), 2.66 (bs, 4H), 3.82 (s, 2H), 3.88 (bs, 2H), 4.02 (bs, 2H), 6.38 (s, 1H), 7.14 (t, J=8.59 Hz, 2H), 7.99-8.09 (m, 2H). Exact mass calculated for Cl17H19FN4O2: 330.2. Found: LCMS m/z=331.3 (M+H+).

Aufarbeitung

  1. customquenched with water
  2. custompurified by preparative HPLC/MS
  3. dissolutionThe resultant lyophilate was dissolved in DCM
  4. additiontreated with MP-carbonate resin (˜100 mg)
  5. stirringThe mixture was stirred for 30 min
  6. filtrationfiltered
  7. customto remove the resin
  8. customThe solvent was removed

Quellen und Nachweise

ORD-Eintrag
ord-9927eeae32824afe95026c1cf9dc8e35
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09434692B2

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