3,5-Dimethoxyaniline → HCID 57625370, compound

HRID 655627Notes

Reaction equation

Cl[C:2]1[C:3]([NH:12][S:13]([C:16]2[S:20][C:19]([C:21]([O:23][CH3:24])=[O:22])=[CH:18][C:17]=2[CH3:25])(=[O:15])=[O:14])=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[CH3:26][O:27][C:28]1[CH:29]=[C:30]([CH:32]=[C:33]([O:35][CH3:36])[CH:34]=1)[NH2:31]>CCO>[CH3:36][O:35][C:33]1[CH:32]=[C:30]([NH:31][C:2]2[C:3]([NH:12][S:13]([C:16]3[S:20][C:19]([C:21]([O:23][CH3:24])=[O:22])=[CH:18][C:17]=3[CH3:25])(=[O:14])=[O:15])=[N:4][C:5]3[C:10]([N:11]=2)=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH:29]=[C:28]([O:27][CH3:26])[CH:34]=1

Participants

Conditions

Temperature: 170 °C

Procedure

Methyl 5-{[(3-chloroquinoxalin-2-yl)amino]sulfonyl}-4-methylthiophene-2-carboxylate (100 mg; 0.25 mmol; 1 eq) and 3,5-dimethoxyaniline (42.35 mg; 0.28 mmol; 1.1 eq) are taken up in EtOH (2 ml) and the resulting suspension is heated up to 170° C. for 6 min on high absorption in the microwave. The precipitate formed is filtered off and washed with EtOH then dried under vacuum at 40° C. for 1 day. The solid is washed with hot EtOH then THF to afford, after cooling at 4° C., 103.6 mg (80%) of the title compound as a powder. 1H NMR (DMSO-d6) δ 12.64 (brs, 1H), 8.91 (s, 1H), 7.89 (brs, 1H), 7.71 (s, 1H), 7.60 (dd, J=7.7, 1.7 Hz, 1H), 7.46-7.34 (m, 2H), 7.32 (d, J=1.9 Hz, 2H), 6.26 (t, J=1.9 Hz, 1H), 3.83 (s, 3H), 3.77 (s, 6H), 2.48 (s, 3H). HPLC (max plot) 95%; Rt 4.93 min. LC/MS: ES+ 515.2, ES− 512.9.

Workup

customThe precipitate formed
filtrationis filtered off
washwashed with EtOH
customthen dried under vacuum at 40° C. for 1 day
washThe solid is washed with hot EtOH
customTHF to afford
temperatureafter cooling at 4° C.

Sources & evidence

ORD record: ord-b80d611a63f54ef4b0f13841ef5906ac
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08071597B2

Reaction notes

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