Diethyl Pyrocarbonate → N-(4-(trifluoromethyl)-2-(piperidin-1-yl)benzyl)-2,3-dihydro-2-oxobenzo[d]oxazole-4-carboxamide

HRID 1505203Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1505203
[O:1]=[C:2]1[NH:6][C:5]2=[C:7]([C:11]([OH:13])=O)[CH:8]=[CH:9][CH:10]=[C:4]2[O:3]1.CCOC(OC(OCC)=O)=O.[F:25][C:26]([F:42])([F:41])[C:27]1[CH:32]=[CH:31][C:30]([CH2:33][NH2:34])=[C:29]([N:35]2[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]2)[CH:28]=1>C1COCC1>[F:41][C:26]([F:25])([F:42])[C:27]1[CH:32]=[CH:31][C:30]([CH2:33][NH:34][C:11]([C:7]2[CH:8]=[CH:9][CH:10]=[C:4]3[O:3][C:2](=[O:1])[NH:6][C:5]=23)=[O:13])=[C:29]([N:35]2[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]2)[CH:28]=1

Komponenten

5

Edukt 3

HCID 3051Diethyl PyrocarbonateHCID 109210912-Oxo-2,3-dihydro-1,3-benzoxazole-4-carboxylic acidHCID 58873623(4-(Trifluoromethyl)-2-(piperidin-1-yl)phenyl)-methanamine

Produkt 1

HCID 53476934N-(4-(trifluoromethyl)-2-(piperidin-1-yl)benzyl)-2,3-dihydro-2-oxobenzo[d]oxazole-4-carboxamideAusbeute 19,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

2,3-dihydro-2-oxobenzo[d]oxazole-4-carboxylic acid 21 (560 mg, 3.1 mmol) was dissolved in 20 ml of THF and at 0° C. DEPC (0.55 ml, 1.2 equiv) and amine 2c (964 mg, 1.2 equiv.) were added to the solution. The mixture was warmed at 80° C. overnight, then evaporated and the crude was dissolved in AcOEt (30 ml) and washed with water (1×20 ml) and brine. The organic phase was dried over sodium sulfate and concentrated under vacuum. The purification of the crude residue by chromatographic column using AcOEt 4/petroleum ether 6 as eluant gave 250 mg of a pale yellow solid. Yield=19% 1HNMR (DMSO, 200 MHz) δ 4.58 (2H, d, J=5.8 Hz), 7.14 (1H, t, J=8 Hz), 7.41 (4H, m), 7.68 (1H, dd, J=8 Hz, J′=0.8 Hz), 9.20 (1H, bt), 11.59 (1H, bs); [M+1] 420.2 (C21H20F3N3O3 requires 419.4).

Aufarbeitung

  1. customevaporated
  2. dissolutionthe crude was dissolved in AcOEt (30 ml)
  3. washwashed with water (1×20 ml) and brine
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. concentrationconcentrated under vacuum
  6. customThe purification of the crude residue by chromatographic column

Quellen und Nachweise

ORD-Eintrag
ord-3a51ea9d376f4d6ba0dd798276c379d9
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09216975B2

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