1,2-Dichloroethane → n-(4-Chloro-3-quinoxalin-2-yl-phenyl)-4-methanesulfonyl-benzamide

HRID 2389260Notes

Reaction equation

[CH3:1][S:2]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=O)=[CH:7][CH:6]=1)(=[O:4])=[O:3].[CH2:14]([Cl:17])[CH2:15]Cl.CCN(C(C)C)C(C)C.Cl[C:28]1[CH:29]=[C:30](O)[C:31]2[N:35]=N[NH:33][C:32]=2[CH:36]=1.[NH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>>[Cl:17][C:14]1[CH:15]=[CH:44][C:39]([NH:38][C:9](=[O:11])[C:8]2[CH:7]=[CH:6][C:5]([S:2]([CH3:1])(=[O:3])=[O:4])=[CH:13][CH:12]=2)=[CH:40][C:41]=1[C:42]1[CH:43]=[N:35][C:31]2[C:32](=[CH:36][CH:28]=[CH:29][CH:30]=2)[N:33]=1

Participants

Reactant 5

HCID 111,2-Dichloroethane

HCID 6115Aniline

HCID 77670p-(Methylsulphonyl)benzoic acid

HCID 81531Diisopropylethylamine

HCID 178516184HCID 178516184, compound

Product 1

HCID 59826481n-(4-Chloro-3-quinoxalin-2-yl-phenyl)-4-methanesulfonyl-benzamideYield 52.2%

Procedure

Procedure D was performed using 4-(methylsulfonyl)benzoic acid (102 mg, 0.49 mmol), EDC (186 mg, 0.93 mmol), DIPEA (0.16 ml, 0.93 mmol), 6-chloro-hydroxybenzotriazole (162 mg, 0.93 mmol) and aniline (119 mg, 0.46 mmol). The crude product was purified by flash column chromatography on silica gel eluting with EtOAc:hexanes (0:1 to 3:2) to afford the desired 4-chloro-3-quinoxalin-2-yl-phenylamine (104 mg, 0.24 mmol).

Workup

customThe crude product was purified by flash column chromatography on silica gel eluting with EtOAc:hexanes (0:1 to 3:2)

Sources & evidence

ORD record: ord-1d0293db9972459ea0b5d7939f287d9c
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08273743B2

Reaction notes

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