2-Amino-5,10-dihydro-dibenzo[b,e][1,4]diazepin-11-one → N-(11-Oxo-10,11-dihydro-5H-dibenzo[b,e][1,4]diazepin-2-yl)-thiophene-2-carboxamidine hydrobromide

HRID 895985Notes

Reaction equation

HRID 895985 reaction equation
[NH2:1][C:2]1[CH:17]=[CH:16][C:5]2[NH:6][C:7]3[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=3[NH:9][C:10](=[O:11])[C:4]=2[CH:3]=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:11]=[C:10]1[NH:9][C:8]2[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=2[NH:6][C:5]2[CH:16]=[CH:17][C:2]([NH:1][C:26]([C:28]3[S:29][CH:30]=[CH:31][CH:32]=3)=[NH:27])=[CH:3][C:4]1=2

Participants

4

Reactant 2

HCID 107755612-Amino-5,10-dihydro-dibenzo[b,e][1,4]diazepin-11-oneHCID 66912440Thiophene-2-carboximidothioic acid phenyl ester hydrobromide

Product 1

HCID 178419709N-(11-Oxo-10,11-dihydro-5H-dibenzo[b,e][1,4]diazepin-2-yl)-thiophene-2-carboxamidine hydrobromide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-Amino-5,10-dihydro-dibenzo[b,e][1,4]diazepin-11-one (Example 6, 54 mg, 0.24 mmol) was dissolved in methanol (10 mL) and thiophene-2-carboximidothioic acid phenyl ester hydrobromide (79 mg, 0.26 mmol) added. The reaction was stirred at room temperature for 4 hr. The solvent was evaporated and the residue recrystallized from a mixture of methanol and ether to give a yellow solid. The solid was washed several times with ether (84 mg, 0.20, 84%).

Workup

  1. customThe solvent was evaporated
  2. customthe residue recrystallized from a mixture of methanol and ether
  3. customto give a yellow solid
  4. washThe solid was washed several times with ether (84 mg, 0.20, 84%)

Sources & evidence

ORD record
ord-8aad96d8e0dc40f2b3f5610d8e1fca31
Source dataset
uspto-grants-2005_07
Patent number
US06919328B1

Reaction notes

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