2,6-Dimethylaniline → HCID 68603262, compound

HRID 1486007Notes

Reaction equation

HRID 1486007 reaction equation
[Cl:1][C:2]1[C:10]([C:11]2[CH:12]=[N:13][C:14]([C:19]([F:22])([F:21])[F:20])=[CH:15][C:16]=2[C:17]#[N:18])=[CH:9][C:5]([C:6](Cl)=[O:7])=[C:4]([O:23][CH3:24])[CH:3]=1.C(N(CC)CC)C.[CH3:32][C:33]1[CH:39]=[CH:38][CH:37]=[C:36]([CH3:40])[C:34]=1[NH2:35]>C(Cl)Cl>[Cl:1][C:2]1[C:10]([C:11]2[CH:12]=[N:13][C:14]([C:19]([F:22])([F:21])[F:20])=[CH:15][C:16]=2[C:17]#[N:18])=[CH:9][C:5]([C:6]([NH:35][C:34]2[C:36]([CH3:40])=[CH:37][CH:38]=[CH:39][C:33]=2[CH3:32])=[O:7])=[C:4]([O:23][CH3:24])[CH:3]=1

Participants

5

Reactant 3

HCID 68962,6-DimethylanilineHCID 8471TriethylamineHCID 86642579HCID 86642579, compound

Product 1

HCID 68603262HCID 68603262, compoundYield 62.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 4-chloro-2-methoxy-5-(4-cyano-6-trifluoromethyl-pyridin-3-yl)-benzoyl chloride (70 mg, 0.19 mmol) in DCM (0.5 mL) were added triethylamine (39 μL, 0.28 mmol) and 2,6-dimethylaniline (28 μL, 0.22 mmol). The mixture was stirred at rt for 12 hrs and was purified via a prep TLC plate eluting with ethyl acetate in hexane (30%) to give 4-chloro-5-(4-cyano-6-trifluoromethyl-pyridin-3-yl)-N-(2,6-dimethyl-phenyl)-2-methoxy-benzamide (55.0 mg). MS [M+H]+ 460.2; tR=2.85 min (method 1)

Workup

  1. customwas purified via a prep TLC plate
  2. washeluting with ethyl acetate in hexane (30%)

Sources & evidence

ORD record
ord-f9e5a8ecbdcd4450b17e57ed5f34a2b4
Source dataset
uspto-grants-2016_08
Patent number
US09422310B2

Reaction notes

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