Hydrochloric Acid → 5-[4-(Isopropylcarbonylamino)phenyl]-1,5,8,9,10,11-hexahydronaphtho[1,2-b][1,4]diazepine-2,4-dione

HRID 1852506Notes

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[CH2:18][CH2:19][CH2:20][CH2:21][C:22]=4[CH:23]=[CH:24][C:9]2=3)=[CH:4][CH:3]=1.[C:25](Cl)(=[O:29])[CH:26]([CH3:28])[CH3:27].Cl>N1C=CC=CC=1>[CH:26]([C:25]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:14](=[O:15])[CH2:13][C:12](=[O:16])[NH:11][C:10]3[C:17]4[CH2:18][CH2:19][CH2:20][CH2:21][C:22]=4[CH:23]=[CH:24][C:9]2=3)=[CH:6][CH:7]=1)=[O:29])([CH3:28])[CH3:27]

Participants

Conditions

Temperature: 80 °C

Procedure

To a pyridine solution (0.5 mL) of 5-(4-aminophenyl)-1,5,8,9,10,11-hexahydronaphtho[1,2-b][1,4]diazepine-2,4-dione (20 mg, 0.062 mmol) obtained in Example 10 was added isobutyryl chloride (10 μL, 0.093 mmol). The mixture was stirred at 80° C. for 1 hour. To the reaction mixture was added aqueous solution of hydrochloric acid under cooling in ice-bath. The mixture was stirred for 20 minutes. Insoluble was collected by filtration, and washed with water. The residue was purified by silica gel column chromatography (chloroform/methanol=99/1) to give the titled compound as white powder (23 mg, yield 95%).

Workup

temperatureunder cooling in ice-bath
stirringThe mixture was stirred for 20 minutes
filtrationInsoluble was collected by filtration
washwashed with water
customThe residue was purified by silica gel column chromatography (chloroform/methanol=99/1)

Sources & evidence

ORD record: ord-8a92a415226e487f854fe7b3e74fdbe9
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962613B2

Reaction notes

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