Dimethylamine → Ethyl 5-(4-chlorophenyl)-4-((dimethylamino)methyl)-3-(4-(N-((dimethylamino)methylene)sulfamoyl)phenyl)thiophene-2-carboxylate

HRID 1053264Notes

Reaction equation

Br[CH2:2][C:3]1[C:4]([C:20]2[CH:25]=[CH:24][C:23]([S:26](=[O:33])(=[O:32])[N:27]=[CH:28][N:29]([CH3:31])[CH3:30])=[CH:22][CH:21]=2)=[C:5]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[S:6][C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=1.[CH3:34][NH:35][CH3:36]>C1C=CC=CC=1>[Cl:14][C:11]1[CH:10]=[CH:9][C:8]([C:7]2[S:6][C:5]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:4]([C:20]3[CH:21]=[CH:22][C:23]([S:26](=[O:33])(=[O:32])[N:27]=[CH:28][N:29]([CH3:31])[CH3:30])=[CH:24][CH:25]=3)[C:3]=2[CH2:2][N:35]([CH3:36])[CH3:34])=[CH:13][CH:12]=1

Participants

Conditions

Temperature: 25 °C

Procedure

To a stirred suspension of Ethyl 4-(bromomethyl)-5-(4-chlorophenyl)-3-(4-(N-((dimethylamino)methylene)sulfamoyl)phenyl)thiophene-2-carboxylate (compound 35b, 2.20 g, 3.86 mmol) in benzene (30 ml), dimethyl amine (0.69 g, 7.6 ml 2M solution in THF, 15.4 mmol) was added at 0° C. in a drop wise manner. The reaction mixture was then stirred at room temperature (about 25° C.) for 16 hr. The progress of the reaction was monitored by TLC. The reaction mixture was then concentrated to obtain the crude product as semi-solid (2.38 g). The crude product so obtained was purified by column chromatography over silica gel (100-200 mesh) using 1.2% methanol in DCM as an eluent to obtain the title compound (1.1 g, 53.39%).

Workup

additionwas added at 0° C. in a drop wise manner
concentrationThe reaction mixture was then concentrated
customto obtain the crude product as semi-solid (2.38 g)
customThe crude product so obtained
customwas purified by column chromatography over silica gel (100-200 mesh)

Sources & evidence

ORD record: ord-e8c644ebe153477098223b7cd3f727d3
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09393247B2

Reaction notes

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