8-amino-5H-benzo[b][1,4]benzoxazepin-6-one → HCID 178419710, compound

HRID 895984Notes

Reaction equation

HRID 895984 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.[BrH:18].C1(S[C:26]([C:28]2[S:29][CH:30]=[CH:31][CH:32]=2)=[NH:27])C=CC=CC=1>CO>[BrH:18].[O:16]=[C:7]1[C:6]2[CH:17]=[C:2]([NH:1][C:26]([C:28]3[S:29][CH:30]=[CH:31][CH:32]=3)=[NH:27])[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 66912440Thiophene-2-carboximidothioic acid phenyl ester hydrobromide

Product 1

HCID 178419710HCID 178419710, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-amino-10H-dibenzo[b,f][1,4]oxazepin-11-one (Example 4, 100 mg, 0.44 mmol) in methanol was added thiophene-2-carboximidothioic acid phenyl ester hydrobromide (146 mg, 0.48 mmol). The mixture was stirred at room temperature for 24 hr. The solvent was evaporated to give a yellow solid that was recrystalized from a mixture of ethanol and diethyl ether to give a yellow solid (yield 50 mg, 43%). H1 NMR (DMSO d6) δ: 11.38 (bs, 1H), 10.67 (s, 1H), 9.77 (bs, 1H), 8.95 (bs, 1H), 8.19-8.18 (m, 1H), 8.10 (s, 1H), 7.85 (s, 1H), 7.71-7.68 (m, 1H), 7.55-7.53 (m, 1H), 7.40-7.43 (m, 2H), 7.21-7.18 (m, 3H).

Workup

  1. customThe solvent was evaporated
  2. customto give a yellow solid
  3. customthat was recrystalized from a mixture of ethanol and diethyl ether

Sources & evidence

ORD record
ord-8b88031cf02741b48b02275c591a8685
Source dataset
uspto-grants-2005_07
Patent number
US06919328B1

Reaction notes

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