Aniline → 5-(4-Phenylcarbamoylphenyl)-1H-naphtho[1,2-b][1,4]diazepine-2,4(3H,5H)-dione

HRID 1049760Notes

Reaction equation

HRID 1049760 reaction equation
[O:1]=[C:2]1[CH2:8][C:7](=[O:9])[N:6]([C:10]2[CH:18]=[CH:17][C:13]([C:14](O)=[O:15])=[CH:12][CH:11]=2)[C:5]2[CH:19]=[CH:20][C:21]3[C:26]([C:4]=2[NH:3]1)=[CH:25][CH:24]=[CH:23][CH:22]=3.CCN=C=NCCCN(C)C.Cl.[CH:39]1[CH:40]=[CH:41][C:42]2N(O)N=[N:45][C:43]=2[CH:44]=1.CN1CCOCC1.NC1C=CC=CC=1>CN(C=O)C>[C:43]1([NH:45][C:14]([C:13]2[CH:12]=[CH:11][C:10]([N:6]3[C:7](=[O:9])[CH2:8][C:2](=[O:1])[NH:3][C:4]4[C:26]5[C:21]([CH:20]=[CH:19][C:5]3=4)=[CH:22][CH:23]=[CH:24][CH:25]=5)=[CH:18][CH:17]=2)=[O:15])[CH:44]=[CH:39][CH:40]=[CH:41][CH:42]=1

Participants

7

Reactant 5

HCID 6115AnilineHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 1176991814-[2,4-Dioxo-3,4-dihydro-1H-naphtho[2,1-b][1,4]diazepin-5(2H)-yl]benzoic acid

Product 1

HCID 1176990985-(4-Phenylcarbamoylphenyl)-1H-naphtho[1,2-b][1,4]diazepine-2,4(3H,5H)-dioneYield 49.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-[2,4-Dioxo-3,4-dihydro-1H-naphtho[2,1-b][1,4]diazepin-5(2H)-yl]benzoic acid (50 mg, 0.144 mmol) obtained in Example 102, (4), WSC.HCl (39 mg, 0.202 mmol), HOBt (31 mg, 0.202 mmol), N-methylmorpholine (47 μL, 0.432 mmol), and aniline (14 L, 0.158 mmol) were stirred at room temperature for 16 hours in anhydrous DMF (1.5 mL). The reaction mixture was post-treated in a conventional manner to give the title compound (30 mg, yield 49%).

Workup

  1. additionThe reaction mixture was post-treated in a conventional manner

Sources & evidence

ORD record
ord-22c883dd9bab41c59b3bbbada43d7307
Source dataset
uspto-grants-2016_07
Patent number
US09382236B2

Reaction notes

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