Benzenamine, 2-chloro-4-(methylsulfonyl)- → 2-[3-chloro-5-(3-chloro-5-cyanophenoxy)phenoxy]-N-[2-chloro-4-(methylsulfonyl)phenyl]acetamide

HRID 1157396Notes

Reaction equation

HRID 1157396 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]=[C:11]([O:13][C:14]2[CH:19]=[C:18]([C:20]#[N:21])[CH:17]=[C:16]([Cl:22])[CH:15]=2)[CH:12]=1)[O:5][CH2:6][C:7](Cl)=[O:8].[Cl:23][C:24]1[CH:30]=[C:29]([S:31]([CH3:34])(=[O:33])=[O:32])[CH:28]=[CH:27][C:25]=1[NH2:26].CCN(C(C)C)C(C)C>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]=[C:11]([O:13][C:14]2[CH:19]=[C:18]([C:20]#[N:21])[CH:17]=[C:16]([Cl:22])[CH:15]=2)[CH:12]=1)[O:5][CH2:6][C:7]([NH:26][C:25]1[CH:27]=[CH:28][C:29]([S:31]([CH3:34])(=[O:33])=[O:32])=[CH:30][C:24]=1[Cl:23])=[O:8]

Participants

5

Reactant 3

HCID 25801Benzenamine, 2-chloro-4-(methylsulfonyl)-HCID 81531DiisopropylethylamineHCID 59511713[3-Chloro-5-(3-chloro-5-cyanophenoxy)phenoxy]acetyl chloride

Product 1

HCID 160449642-[3-chloro-5-(3-chloro-5-cyanophenoxy)phenoxy]-N-[2-chloro-4-(methylsulfonyl)phenyl]acetamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A DMF solution (0.5 mL) of 29 mg (0.081 mmol) of [3-chloro-5-(3-chloro-5-cyanophenoxy)phenoxy]acetyl chloride (5-4), 33 mg (0.163 mmol) of 2-chloro-4-methylsulfonylaniline (5-5) and 21 mg (0.163 mmol) of DIEA were stirred at 25° C. until the reaction would not proceed any further. This solution was loaded directly onto a CombiFlash silica gel column eluted with EtOAc:hexanes (3:97 to 100:0). Clean fractions were combined and concentrated in vacuo to give the desired product 5-6 as a white solid. Rf=0.8 (DCM:MeOH:NH4OH 98:2:0.2). HRMS (M+Na): measured 542.0066; theoretical 542.0105. 1H NMR(CDCl3): 3.07 (s, 3H), 4.69 (s, 2H), 6.61 (m, 1H), 6.74 (m, 1H), 6.89 (m, 1H), 7.15 (m, 1H), 7.25 (m, 1H), 7.42 (m, 1H), 6.94 (dd, 1H), 8.02 (m, 1H), 8.74 (d, 1H), 9.11 (s, 1H).

Workup

  1. washeluted with EtOAc:hexanes (3:97 to 100:0)
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1047dbbc9423428dbf2391661f6901d6
Source dataset
uspto-grants-2010_10
Patent number
US07807684B2

Reaction notes

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