8-amino-5H-benzo[b][1,4]benzoxazepin-6-one → HCID 178465553, Verbindung

HRID 895982Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 895982
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[O:11][C:10]3[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=3[NH:8][C:7](=[O:16])[C:6]=2[CH:17]=1.Br.C1C2C(=CC=CC=2)C=CC=1CS[C:31](=[NH:33])[CH3:32]>C(O)C>[O:16]=[C:7]1[C:6]2[CH:17]=[C:2]([NH:1][C:31](=[NH:33])[CH3:32])[CH:3]=[CH:4][C:5]=2[O:11][C:10]2[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=2[NH:8]1

Komponenten

4

Edukt 2

HCID 27563998-amino-5H-benzo[b][1,4]benzoxazepin-6-oneHCID 221387052-Naphthylmethyl ethanimidothioate hydrobromide

Produkt 1

HCID 178465553HCID 178465553, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a stirred solution of 2-amino-10H-dibenzo[b,f][1,4]oxazepin-11-one (Example 4, 50 mg, 0.22 mmol) in 4 mL of ethanol at 0° C. was added thioacetimidic acid naphthalen-2-ylmethyl ester hydrobromide (65 mg, 0.22 mmol). The reaction was warmed to room temperature overnight. The mixture was concentrated at reduced pressure and partitioned between water (5 mL) and ethyl acetate (25 mL). The aqueous layer was separated and evaporated under vacuum (yield 70 mg, 92%). H1 NMR (DMSO d6) δ: 11.15 (bs, 1H), 10.68 (s, 1H), 9.44 (bs, 1H), 8.56 (bs, 1H), 7.71-7.70 (m, 1H), 7.54-7.53 (m, 2H), 7.40-7.36 (m, 1H), 7.20-7.17 (m, 3H), 2.31 (s, 3H), MS (ES): MH+ 268.3.

Aufarbeitung

  1. concentrationThe mixture was concentrated at reduced pressure
  2. custompartitioned between water (5 mL) and ethyl acetate (25 mL)
  3. customThe aqueous layer was separated
  4. customevaporated under vacuum (yield 70 mg, 92%)

Quellen und Nachweise

ORD-Eintrag
ord-d1e932c3f07547b5934f1964769a7d45
Quelldatensatz
uspto-grants-2005_07
Patentnummer
US06919328B1

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