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

HRID 895982Notes

Reaction equation

HRID 895982 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

HCID 178465553HCID 178465553, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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.

Workup

  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%)

Sources & evidence

ORD record
ord-d1e932c3f07547b5934f1964769a7d45
Source dataset
uspto-grants-2005_07
Patent number
US06919328B1

Reaction notes

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