2-Chloro-3-methoxybenzoyl chloride → N-[4-(2,4-Dioxo-1,2,3,4-tetrahydronaphtho[1,2-b][1,4]diazepin-5-yl)butyl]-2-chloro-3-methoxybenzamide

HRID 1049730Notes

Reaction equation

HRID 1049730 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[C:12](=[O:13])[CH2:11][C:10](=[O:14])[NH:9][C:8]2[C:15]3[C:20]([CH:21]=[CH:22][C:7]1=2)=[CH:19][CH:18]=[CH:17][CH:16]=3.[Cl:23][C:24]1[C:32]([O:33][CH3:34])=[CH:31][CH:30]=[CH:29][C:25]=1[C:26](Cl)=[O:27].CC1C(C)=CC=CC=1C(NC1C=CC(N2C(=O)CC(=O)NC3C4C(C=CC2=3)=CC=CC=4)=CC=1OC)=O>>[O:14]=[C:10]1[NH:9][C:8]2[C:15]3[C:20]([CH:21]=[CH:22][C:7]=2[N:6]([CH2:5][CH2:4][CH2:3][CH2:2][NH:1][C:26](=[O:27])[C:25]2[CH:29]=[CH:30][CH:31]=[C:32]([O:33][CH3:34])[C:24]=2[Cl:23])[C:12](=[O:13])[CH2:11]1)=[CH:19][CH:18]=[CH:17][CH:16]=3

Participants

4

Reactant 3

HCID 216904052-Chloro-3-methoxybenzoyl chlorideHCID 1176990395-[4-(2,3-Dimethylbenzoylamino)-3-methoxyphenyl]-1H-naphtho[1,2-b][1,4]diazepine-2,4(3H,5H)-dioneHCID 1176992895-(4-aminobutyl)-1H-naphtho[2,1-b][1,4]diazepine-2,4(3H,5H)-dione

Product 1

HCID 117699156N-[4-(2,4-Dioxo-1,2,3,4-tetrahydronaphtho[1,2-b][1,4]diazepin-5-yl)butyl]-2-chloro-3-methoxybenzamideYield 56%

Procedure

By using N-(tert-butoxycarbonyl)-1,4-diaminobutane as the starting material, 5-(4-aminobutyl)-1H-naphtho[2,1-b][1,4]diazepine-2,4(3H,5H)-dione was obtained in the same manner as that of Example 42, (1) and (2). By using 5-(4-aminobutyl)-1H-naphtho[2,1-b][1,4]diazepine-2,4(3H,5H)-dione (30 mg, 0.1 mmol), and 2-chloro-3-methoxybenzoyl chloride (0.15 mmol), the title compound (26 mg, yield 56%) was obtained in the same manner as that of Example 1, (4).

Sources & evidence

ORD record
ord-9c6b236e1e354b4e920ca8dbf45abdb1
Source dataset
uspto-grants-2016_07
Patent number
US09382236B2

Reaction notes

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