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

HRID 16179
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 16179
[F:1][C:2]([F:34])([F:33])[C:3]([NH:5][C@H:6]1[C@@H:16]2[N:10]([C:11]3[CH:24]=[C:23]([NH:25]CC4C=CC=CC=4)[CH:22]=[CH:21][C:12]=3[O:13][C:14]3[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=32)[CH2:9][CH2:8][CH2:7]1)=[O:4].Cl.O1CCOCC1>C(O)C.[Pd]>[NH2:25][C:23]1[CH:22]=[CH:21][C:12]2[O:13][C:14]3[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=3[C@@H:16]3[C@H:6]([NH:5][C:3](=[O:4])[C:2]([F:33])([F:34])[F:1])[CH2:7][CH2:8][CH2:9][N:10]3[C:11]=2[CH:24]=1
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Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 86599889trans-2,2,2-trifluoro-N-[2,3,4,14b-tetrahydro-7-[(phenylmethyl)amino]-1H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepin-1-yl]acetamide

Produkt 1

HCID 86599890trans-N-(7-Amino-2,3,4,14b-tetrahydro-1H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepin-1-yl)-2,2,2-trifluoroacetamideAusbeute 53 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938
Palladium
Katalysator
HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of trans-2,2,2-trifluoro-N-[2,3,4,14b-tetrahydro-7-[(phenylmethyl)amino]-1H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepin-1-yl]acetamide (944 mg, 2.0 mmol) in ethanol (16 mL) were added Pd/C 10% (111 mg) and a solution of 4M HCl in dioxane (778 μl, 3.11 mmol). The resulting reaction mixture was hydrogenated at 3 bar for 6 h. The reaction mixture was quenched with sat. NaHCO3 (aq) and diluted with ethanol. After filtration through dicalite and thorough washing with ethyl acetate, the volatiles were removed in vacuo. A part of the crude product was purified with HPLC to afford the title compound (29 mg, 53%). Data (m/z)=378 (M+H)+.

Aufarbeitung

  1. customThe resulting reaction mixture
  2. customThe reaction mixture was quenched with sat. NaHCO3 (aq)
  3. additiondiluted with ethanol
  4. filtrationAfter filtration through dicalite
  5. washthorough washing with ethyl acetate
  6. customthe volatiles were removed in vacuo
  7. customA part of the crude product was purified with HPLC

Quellen und Nachweise

ORD-Eintrag
ord-62780275474946fcb37d7b069485186d
Quelldatensatz
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07737136B2

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