Thiophenol → 5-(4-Methylaminophenyl)-1,5,8,9,10,11-hexahydronaphtho[1,2-b][1,4]diazepine-2,4-dione

HRID 1049821Notes

Reaction equation

HRID 1049821 reaction equation
[O:1]=[C:2]1[NH:8][C:7]2[C:9]3[CH2:10][CH2:11][CH2:12][CH2:13][C:14]=3[CH:15]=[CH:16][C:6]=2[N:5]([C:17]2[CH:22]=[CH:21][C:20]([N:23]([CH3:36])S(C3C=CC=CC=3[N+]([O-])=O)(=O)=O)=[CH:19][CH:18]=2)[C:4](=[O:37])[CH2:3]1.C1(S)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:36][NH:23][C:20]1[CH:19]=[CH:18][C:17]([N:5]2[C:4](=[O:37])[CH2:3][C:2](=[O:1])[NH:8][C:7]3[C:9]4[CH2:10][CH2:11][CH2:12][CH2:13][C:14]=4[CH:15]=[CH:16][C:6]2=3)=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 7969ThiophenolHCID 11430Potassium CarbonateHCID 86689319N-[4-(2,4-Dioxo-1,2,3,4,8,9,10,11-octahydronaphtho[1,2-b][1,4]diazepine-5-yl)phenyl]-N-methyl-2-nitrobenzenesulfonamide

Product 1

HCID 866893205-(4-Methylaminophenyl)-1,5,8,9,10,11-hexahydronaphtho[1,2-b][1,4]diazepine-2,4-dioneYield 55%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-[4-(2,4-Dioxo-1,2,3,4,8,9,10,11-octahydro-naphtho[1,2-b][1,4]diazepin-5-yl)phenyl]-N-methyl-2-nitrobenzenesulfonamide (99 mg, 0.190 mmol) obtained in Example 152, thiophenol (23 μL, 0.228 mmol), potassium carbonate (79 mg, 0.570 mmol), and anhydrous DMF were mixed, and the mixture was stirred at room temperature for 16 hours. After the disappearance of the starting materials was confirmed, a post-treatment was performed in a conventional manner to give the title compound (35 mg, yield 55%).

Sources & evidence

ORD record
ord-634851c9965c42598528bd8a3c12878f
Source dataset
uspto-grants-2016_07
Patent number
US09382236B2

Reaction notes

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