2,3-Dimethoxybenzoyl chloride → 5-[4-(2,3-Dimethoxybenzoylamino)phenyl]1H-naphtho[1,2-b][1,4]diazepine-2,4(3H,5H)-dione

HRID 1049683Notes

Reaction equation

HRID 1049683 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:14](=[O:15])[CH2:13][C:12](=[O:16])[NH:11][C:10]3[C:17]4[C:22]([CH:23]=[CH:24][C:9]2=3)=[CH:21][CH:20]=[CH:19][CH:18]=4)=[CH:4][CH:3]=1.[CH3:25][O:26][C:27]1[C:35]([O:36][CH3:37])=[CH:34][CH:33]=[CH:32][C:28]=1[C:29](Cl)=[O:30].C(NC1C=CC(N2C(=O)CC(=O)NC3C4C(C=CC2=3)=CC=CC=4)=CC=1)(=O)C1C=CC=CC=1>>[CH3:25][O:26][C:27]1[C:35]([O:36][CH3:37])=[CH:34][CH:33]=[CH:32][C:28]=1[C:29]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:14](=[O:15])[CH2:13][C:12](=[O:16])[NH:11][C:10]3[C:17]4[C:22]([CH:23]=[CH:24][C:9]2=3)=[CH:21][CH:20]=[CH:19][CH:18]=4)=[CH:4][CH:3]=1)=[O:30]

Participants

4

Reactant 3

HCID 27583922,3-Dimethoxybenzoyl chlorideHCID 716569715-(4-Benzoylaminophenyl)-1H-naphtho[1,2-b][1,4]diazepine-2,4(3H,5H)-dioneHCID 1176991675-(4-Aminophenyl)-1H-naphtho[1,2-b][1,4]diazepine-2,4(3H,5H)-dione

Product 1

HCID 1176991465-[4-(2,3-Dimethoxybenzoylamino)phenyl]1H-naphtho[1,2-b][1,4]diazepine-2,4(3H,5H)-dioneYield 55%

Procedure

By using 5-(4-aminophenyl)-1H-naphtho[1,2-b][1,4]diazepine-2,4(3H,5H)-dione (100 mg, 0.315 mmol) obtained in Example 1, (3), and 2,3-dimethoxybenzoyl chloride (0.473 mmol), the title compound (83 mg, yield 55%) was obtained in the same manner as that of Example 1, (4).

Sources & evidence

ORD record
ord-1ec3fc64ef824563b48ad02dbc3b951d
Source dataset
uspto-grants-2016_07
Patent number
US09382236B2

Reaction notes

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