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Hydrochloric Acid → trans-N-(7-Acetyl-2,3,4,14b-tetrahydro-1H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepin-1-yl)-2,2,2-trifluoroacetamide

HRID 16177
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 16177
[CH2:1]([O:3]C([Sn](CCCC)(CCCC)CCCC)=C)[CH3:2].Br[C:20]1[CH:45]=[CH:44][C:23]2[O:24][C:25]3[CH:43]=[CH:42][CH:41]=[CH:40][C:26]=3[C@@H:27]3[C@H:32]([NH:33][C:34](=[O:39])[C:35]([F:38])([F:37])[F:36])[CH2:31][CH2:30][CH2:29][N:28]3[C:22]=2[CH:21]=1.Cl>C1(C)C=CC=CC=1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:1]([C:20]1[CH:45]=[CH:44][C:23]2[O:24][C:25]3[CH:43]=[CH:42][CH:41]=[CH:40][C:26]=3[C@@H:27]3[C@H:32]([NH:33][C:34](=[O:39])[C:35]([F:36])([F:38])[F:37])[CH2:31][CH2:30][CH2:29][N:28]3[C:22]=2[CH:21]=1)(=[O:3])[CH3:2]
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Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 86599888trans-N-(7-bromo-2,3,4,14b-tetrahydro-1H-dibenzo[b,f]pyrido[1,2-d][1,4]-oxazepin-1-yl)-2,2,2-trifluoroacetamide

Produkt 1

HCID 86599887trans-N-(7-Acetyl-2,3,4,14b-tetrahydro-1H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepin-1-yl)-2,2,2-trifluoroacetamideAusbeute 47 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

(1-Ethoxyvinyl)tributyl tin (90 μl, 0.23 mmol) was added to a solution of trans-N-(7-bromo-2,3,4,14b-tetrahydro-1H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepin-1-yl)-2,2,2-trifluoroacetamide (100 mg, 0.23 mmol) and PdCl2(PPh3)2 (3 mg, 4.3 μmol) in toluene (6 mL) under N2. The reaction mixture was heated to 140° C. and stirred for 3 h. After cooling to room temperature, 2N (aq) HCl (450 ul) was added and the reaction mixture was stirred for 1 h. The reaction was quenched with sat NaHCO3 (aq) and extracted with ethyl acetate. The organic layer was washed with brine, dried (Na2SO4) and evaporated. The crude compound was chromatographed with heptane/ethyl acetate 1:1. Purifcation by HPLC gave the title compound (43 mg, 47%). Data: 1H-NMR (400 MHz, DMSO) 1.60-2.09 (m, 4H), 3.21 (t, J=11.2, 1H), 3.90 (d, J=14.0, 1H), 4.16 (d, J=10.4, 1H), 4.44 (m, 1H), 7.04-7.54 (m, 10H), 9.20 (d, J=10.0, 1H). (m/z)=405 (M+H)+.

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. stirringthe reaction mixture was stirred for 1 h
  3. customThe reaction was quenched with sat NaHCO3 (aq)
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried (Na2SO4)
  7. customevaporated
  8. customThe crude compound was chromatographed with heptane/ethyl acetate 1:1

Quellen und Nachweise

ORD-Eintrag
ord-f91f3165350549bfa6009c4f389ece63
Quelldatensatz
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07737136B2

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