Triethylamine → 3-(2,5-Difluoro-phenyl)-N-{1-[3-(pyridin-4-ylamino)-phenyl]ethyl}-acrylamide

HRID 2183472Notes

Reaction equation

HRID 2183472 reaction equation
[NH2:1][C@H:2]([C:4]1[CH:5]=[C:6]([NH:10][C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)[CH:7]=[CH:8][CH:9]=1)[CH3:3].[F:17][C:18]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][C:19]=1[CH:20]=[C:21](Cl)[C:22](O)=[O:23].CCN=C=NCCCN(C)C.Cl.C(N(CC)CC)C>CN(C1C=CN=CC=1)C.ClCCl>[F:17][C:18]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][C:19]=1[CH:20]=[CH:21][C:22]([NH:1][CH:2]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([NH:10][C:11]2[CH:12]=[CH:13][N:14]=[CH:15][CH:16]=2)[CH:5]=1)[CH3:3])=[O:23]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 60004117(S)-[3-(1-amino-ethyl)-phenyl]-pyridin-4-yl-amineHCID 867597472.5-Difluoro-chlorocinnamic acid

Product 1

HCID 698003043-(2,5-Difluoro-phenyl)-N-{1-[3-(pyridin-4-ylamino)-phenyl]ethyl}-acrylamideYield 81.7%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of (S)-[3-(1-amino-ethyl)-phenyl]-pyridin-4-yl-amine (0.1 mmol), 2.5-difluoro-chlorocinnamic acid (0.1 mmol), EDAC.HCl (0.2 mmol), DMAP (0.1 mmol), triethylamine (0.3 mmol) in dichloromethane (2 mL) was stirred at room temperature overnight. The reaction mixture was purified by flash chromatography with 5% methnol in ethyl acetate to provide the title compound (31 mg) as a solid.

Workup

  1. customThe reaction mixture was purified by flash chromatography with 5% methnol in ethyl acetate

Sources & evidence

ORD record
ord-516a3a37db3a4d388f037877ad273a50
Source dataset
uspto-grants-2005_05
Patent number
US06900210B2

Reaction notes

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