Diethyl squarate → 3-[4-Chloro-2-hydroxy-3-(4-methylpiperazine-1-sulfonyl)phenylamino]-4-ethoxycyclobut-3-ene-1,2-dione

HRID 1050989Notes

Reaction equation

[NH2:1][C:2]1[C:7]([OH:8])=[C:6]([S:9]([N:12]2[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]2)(=[O:11])=[O:10])[C:5]([Cl:19])=[CH:4][CH:3]=1.[CH2:20]([O:22][C:23]1[C:24](=O)[C:25](=[O:30])[C:26]=1[O:27]CC)[CH3:21]>C(O)C>[Cl:19][C:5]1[CH:4]=[CH:3][C:2]([NH:1][C:24]2[C:25](=[O:30])[C:26](=[O:27])[C:23]=2[O:22][CH2:20][CH3:21])=[C:7]([OH:8])[C:6]=1[S:9]([N:12]1[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]1)(=[O:11])=[O:10]

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 1.98 g (6.5 mmol, 1 eq) of 6-amino-3-chloro-2-(4-methylpiperazine-1-sulfonyl)phenol and 2.20 g (48.8 mmol, 2 eq) of 3,4-diethoxy-3-cyclobutene-1,2-dione was placed in solution in 20 ml of ethanol. The reaction medium was heated at 50° C. for 16 hours. The insoluble material was filtered off, washed with ethanol and dried under vacuum at 45° C. 2.05 g of 3-[4-chloro-2-hydroxy-3-(4-methylpiperazine-1-sulfonyl)phenylamino]-4-ethoxycyclobut-3-ene-1,2-dione were obtained in the form of a yellow solid. Yield=74%.

Workup

filtrationThe insoluble material was filtered off
washwashed with ethanol
customdried under vacuum at 45° C

Sources & evidence

ORD record: ord-c5a1ef9db07945ea9c26e88ba5415c2d
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09388149B2

Reaction notes

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