2-Chloro-6-methoxybenzoyl chloride → 5-[4-(2-Chloro-6-methoxybenzoylamino)phenyl]-1,3-dihydronaphtho[1,2-e]-1,4-diazepin-2-one

HRID 1049777Notes

Reaction equation

HRID 1049777 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]3[CH:23]=[CH:22][C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[C:10]=3[NH:11][C:12](=[O:15])[CH2:13][N:14]=2)=[CH:4][CH:3]=1.[Cl:24][C:25]1[CH:33]=[CH:32][CH:31]=[C:30]([O:34][CH3:35])[C:26]=1[C:27](Cl)=[O:28].NC1C=CC(N2C(=O)CC(=O)NC3C(CC)=CC=CC2=3)=CC=1>>[Cl:24][C:25]1[CH:33]=[CH:32][CH:31]=[C:30]([O:34][CH3:35])[C:26]=1[C:27]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:9]3[CH:23]=[CH:22][C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[C:10]=3[NH:11][C:12](=[O:15])[CH2:13][N:14]=2)=[CH:6][CH:7]=1)=[O:28]

Participants

4

Reactant 3

HCID 128926772-Chloro-6-methoxybenzoyl chlorideHCID 1176991231-(4-Aminophenyl)-6-ethyl-1H-benzo[b][1,4]diazepine-2,4(3H,5H)-dioneHCID 1176991615-(4-Aminophenyl)-1H-naphtho[1,2-e][1,4]diazepin-2(3H)-one

Product 1

HCID 1176990435-[4-(2-Chloro-6-methoxybenzoylamino)phenyl]-1,3-dihydronaphtho[1,2-e]-1,4-diazepin-2-oneYield 83.5%

Procedure

By using 5-(4-aminophenyl)-1,3-dihydronaphtho[1,2-e]-1,4-diazepin-2-one (40 mg, 0.13 mmol) obtained in Example 64, and 2-chloro-6-methoxybenzoyl chloride (0.2 mmol), the title compound (51 mg, yield 54%) was obtained in the same manner as that of Example 1, (4).

Sources & evidence

ORD record
ord-f12897e1478c4b39b64188d147801952
Source dataset
uspto-grants-2016_07
Patent number
US09382236B2

Reaction notes

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