Trifluoroacetic acid → N-[(4aR,11bR)-2-amino-3,3,11b-trimethyl-4,4-dioxo-5,6-dihydro-4aH-[1]benzoxepino[4,5-b][1,4]thiazin-10-yl]-5-chloro-3-methylpyridine-2-carboxamide

HRID 627740Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 627740
[Cl:1][C:2]1[CH:3]=[C:4]([CH3:39])[C:5]([C:8]([NH:10][C:11]2[CH:12]=[CH:13][C:14]3[O:36][CH2:35][CH2:34][C@H:17]4[S:18](=[O:33])(=[O:32])[C:19]([CH3:31])([CH3:30])[C:20]([NH:22]C(=O)OC(C)(C)C)=[N:21][C@:16]4([CH3:37])[C:15]=3[CH:38]=2)=[O:9])=[N:6][CH:7]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:22][C:20]1[C:19]([CH3:31])([CH3:30])[S:18](=[O:32])(=[O:33])[C@@H:17]2[CH2:34][CH2:35][O:36][C:14]3[CH:13]=[CH:12][C:11]([NH:10][C:8](=[O:9])[C:5]4[C:4]([CH3:39])=[CH:3][C:2]([Cl:1])=[CH:7][N:6]=4)=[CH:38][C:15]=3[C@@:16]2([CH3:37])[N:21]=1

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 90308596tert-butyl ((4aR,11bR)-10-(5-chloro-3-methylpicolinamido)-3,3,11b-trimethyl-4,4-dioxido-4a,5,6,11b-tetrahydro-3H-benzo[6,7]oxepino[4,5-b][1,4]thiazin-2-yl)carbamate

Produkt 1

HCID 90308598N-[(4aR,11bR)-2-amino-3,3,11b-trimethyl-4,4-dioxo-5,6-dihydro-4aH-[1]benzoxepino[4,5-b][1,4]thiazin-10-yl]-5-chloro-3-methylpyridine-2-carboxamideAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of trans-isomer tert-butyl ((4aR,11bR)-10-(5-chloro-3-methylpicolinamido)-3,3,11b-trimethyl-4,4-dioxido-4a,5,6,11b-tetrahydro-3H-benzo[6,7]oxepino[4,5-b][1,4]thiazin-2-yl)carbamate (110 mg, 0.191 mmol) in DCM (2 ml) was treated with TFA (0.7 ml, 9.53 mmol) for 10 min at RT. The mixture was concentrated to dryness, redissolved in 0.5 ml of MeOH and neutralized with saturated solution NaHCO3. Precipitated material was extracted with ethyl acetate, organic extract was washed with water, brine, filtered through pad of celite and concentrated to afford N-((4aR,11bR)-2-amino-3,3,11b-trimethyl-4,4-dioxido-4a,5,6,11b-tetrahydro-3H-benzo[6,7]oxepino[4,5-b][1,4]thiazin-10-yl)-5-chloro-3-methylpicolinamide (89 mg, 0.187 mmol, 98% yield). LC/MS (ESI+) m/z=477.

Aufarbeitung

  1. concentrationThe mixture was concentrated to dryness
  2. dissolutionredissolved in 0.5 ml of MeOH and neutralized with saturated solution NaHCO3
  3. extractionPrecipitated material was extracted with ethyl acetate
  4. extractionorganic extract
  5. washwas washed with water, brine
  6. filtrationfiltered through pad of celite
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-a4875ba48d344dd1a8223ffd8a958582
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09309263B2

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