Triethylamine → N-(Biphenyl-4-ylmethyl)-3,5-dichloro-N-(3-((4-cyanophenylsulfonamido)methyl)benzyl)-2-hydroxybenzenesulfonamide

HRID 1889619Notes

Reaction equation

[C:1]([C:3]1[CH:8]=[CH:7][C:6]([S:9](Cl)(=[O:11])=[O:10])=[CH:5][CH:4]=1)#[N:2].CCN(CC)CC.[NH2:20][CH2:21][C:22]1[CH:23]=[C:24]([CH:52]=[CH:53][CH:54]=1)[CH2:25][N:26]([CH2:39][C:40]1[CH:45]=[CH:44][C:43]([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)=[CH:42][CH:41]=1)[S:27]([C:30]1[CH:35]=[C:34]([Cl:36])[CH:33]=[C:32]([Cl:37])[C:31]=1[OH:38])(=[O:29])=[O:28]>C(Cl)Cl>[C:43]1([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[CH:44]=[CH:45][C:40]([CH2:39][N:26]([CH2:25][C:24]2[CH:52]=[CH:53][CH:54]=[C:22]([CH2:21][NH:20][S:9]([C:6]3[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=3)(=[O:11])=[O:10])[CH:23]=2)[S:27]([C:30]2[CH:35]=[C:34]([Cl:36])[CH:33]=[C:32]([Cl:37])[C:31]=2[OH:38])(=[O:29])=[O:28])=[CH:41][CH:42]=1

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of 4-cyanobenzene-1-sulfonyl chloride (26 mg, 0.13 mmol) in CH2Cl2 (3 ml) was added Et3N (0.07 ml, 0.49 mmol) followed by N-(3-(aminomethyl)benzyl)-N-(biphenyl-4-ylmethyl)-3,5-dichloro-2-hydroxybenzenesulfonamide (65 mg, 0.12 mmol) at rt under nitrogen. The reaction mixture was stirred at 25° C. for 2 h. It was concentrated and the residue was purified by preparative HPLC. Fractions containing the desired product were combined, concentrated, and lyophilized to give the product as a white solid (50 mg, 56%).

Workup

concentrationIt was concentrated
customthe residue was purified by preparative HPLC
additionFractions containing the desired product
concentrationconcentrated

Sources & evidence

ORD record: ord-e038c49ad2014672ae85f97496557b92
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501992B2

Reaction notes

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