Methyl 3-amino-4-chloro-2-((3-hydroxypropyl)amino]benzoate → Methyl 4-chloro-3-{[(2,6-dibromo-4-hydroxyphenyl)carbamothioyl]amino}-2-[(3-hydroxypropyl)amino]benzoate

HRID 1628557Notes

Reaction equation

[NH2:1][C:2]1[C:3]([NH:13][CH2:14][CH2:15][CH2:16][OH:17])=[C:4]([CH:9]=[CH:10][C:11]=1[Cl:12])[C:5]([O:7][CH3:8])=[O:6].[Br:18][C:19]1[CH:24]=[C:23]([O:25]C)[CH:22]=[C:21]([Br:27])[C:20]=1[N:28]=[C:29]=[S:30]>CN(C)C1C=CN=CC=1>[Cl:12][C:11]1[CH:10]=[CH:9][C:4]([C:5]([O:7][CH3:8])=[O:6])=[C:3]([NH:13][CH2:14][CH2:15][CH2:16][OH:17])[C:2]=1[NH:1][C:29](=[S:30])[NH:28][C:20]1[C:21]([Br:27])=[CH:22][C:23]([OH:25])=[CH:24][C:19]=1[Br:18]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of methyl 3-amino-4-chloro-2-[(3-hydroxypropyl)amino]benzoate (1.00 g, 3.87 mmol), 1,3-dibromo-2-isothiocyanato-5-methoxybenzene (1.50 g, 4.64 mmol) and catalytic amount of 4-dimethylaminopyridine was stirred at 80° C. for 16 h and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with a 30-70% ethyl acetate/n-hexane gradient mixture to give the title compound as a brown oil (560 mg, 0.963 mmol, 25%).

Workup

concentrationconcentrated in vacuo
customThe residue was purified by flash column chromatography on silica gel eluting with a 30-70% ethyl acetate/n-hexane gradient mixture

Sources & evidence

ORD record: ord-6245b6dff7344102820563e9dce5b5d8
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08785460B2

Reaction notes

Loading…