4-(4-Ethylpiperazin-1-yl)aniline → HCID 67199000, compound

HRID 591211Notes

Reaction equation

[CH2:1]([N:3]1[CH2:8][CH2:7][N:6]([C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=2)[CH2:5][CH2:4]1)[CH3:2].Cl[C:17]1([C:41]2[C:42]([O:47][CH2:48][CH3:49])=[N:43][CH:44]=[CH:45][CH:46]=2)[C:25]2[C:20](=[CH:21][CH:22]=[C:23]([I:26])[CH:24]=2)[N:19]([S:27]([C:30]2[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][C:31]=2[O:38][CH3:39])(=[O:29])=[O:28])[C:18]1=[O:40]>ClCCl>[CH3:39][O:38][C:31]1[CH:32]=[C:33]([O:36][CH3:37])[CH:34]=[CH:35][C:30]=1[S:27]([N:19]1[C:20]2[C:25](=[CH:24][C:23]([I:26])=[CH:22][CH:21]=2)[C:17]([C:41]2[C:42]([O:47][CH2:48][CH3:49])=[N:43][CH:44]=[CH:45][CH:46]=2)([NH:15][C:12]2[CH:13]=[CH:14][C:9]([N:6]3[CH2:5][CH2:4][N:3]([CH2:1][CH3:2])[CH2:8][CH2:7]3)=[CH:10][CH:11]=2)[C:18]1=[O:40])(=[O:29])=[O:28]

Participants

Conditions

Temperature: 120 °C

Procedure

4-(4-Ethylpiperazin-1-yl)phenylamine (44 mg, 0.21 mmol) was added to a solution of 3-chloro-1-(2,4-dimethoxyphenylsulfonyl)-3-(2-ethoxypyridin-3-yl)-5-iodo-1,3-dihydro-indol-2-one (110 mg, 0.18 mmol) in dichloromethane (15 ml). The reaction mixture was agitated in a Biotage microwave vial at 120° C. for 4 hours. The reaction mixture was concentrated under reduced pressure. Purification by chromatography (silica gel, 0-8% methanol in dichloromethane) resulted in 16 mg of the title compound (11% yield).

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
customPurification by chromatography (silica gel, 0-8% methanol in dichloromethane)

Sources & evidence

ORD record: ord-840970520f614d05bdfb51a4c6a50f15
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09238642B2

Reaction notes

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