Triethylamine → 5-(2,4-Dichloro-phenyl)-penta-2,4-dienoic acid [3-(4-chloro-phenyl)-allyl]-(3,4-difluoro-benzyl)-amide

HRID 597879Notes

Reaction equation

HRID 597879 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH:9][CH2:10][NH:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([F:19])=[C:15]([F:20])[CH:14]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[Cl:28][C:29]1[CH:34]=[C:33]([Cl:35])[CH:32]=[CH:31][C:30]=1[CH:36]=[CH:37][CH:38]=[CH:39][C:40](Cl)=[O:41]>CN(C1C=CN=CC=1)C.ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]=[CH:9][CH2:10][N:11]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([F:19])=[C:15]([F:20])[CH:14]=2)[C:40](=[O:41])[CH:39]=[CH:38][CH:37]=[CH:36][C:30]2[CH:31]=[CH:32][C:33]([Cl:35])=[CH:34][C:29]=2[Cl:28])=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 67271292[3-(4-Chloro-phenyl)-allyl]-(3,4-difluoro-benzyl)-amineHCID 724729475-(2,4-Dichloro-phenyl)-penta-2,4-dienoyl chloride

Product 1

HCID 724729225-(2,4-Dichloro-phenyl)-penta-2,4-dienoic acid [3-(4-chloro-phenyl)-allyl]-(3,4-difluoro-benzyl)-amideYield 77.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of [3-(4-chloro-phenyl)-allyl]-(3,4-difluoro-benzyl)-amine (1.49 g, 5.1 mmol), triethylamine (1.06 mL, 7.6 mmol, 1.5 eq.), DMAP (i.e., dimethylaminopyridine) (62 mg, 0.51 mmol, 0.1 eq.) in 15 mL dichloromethane at 0° C. was added a solution of 5-(2,4-dichloro-phenyl)-penta-2,4-dienoyl chloride (6.3 mmol) in 15 mL dichloromethane and stirred for 1 hr. After aqueous work-up, the crude product was purified by chromatography with 20% ethyl acetate-hexanes to provide 2.05 g of 5-(2,4-dichloro-phenyl)-penta-2,4-dienoic acid [3-(4-chloro-phenyl)-allyl]-(3,4-difluoro-benzyl)-amide.

Workup

  1. customAfter aqueous work-up, the crude product was purified by chromatography with 20% ethyl acetate-hexanes

Sources & evidence

ORD record
ord-b5a293f1f6f549b5a59c0f4b929c0679
Source dataset
uspto-grants-2011_03
Patent number
US07897601B2

Reaction notes

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