Triethylamine → (+/-)-N-[1-(2-Fluoro-5-morpholin-4-yl-phenyl)ethyl]-3-(2-fluoro-phenyl)acrylamide

HRID 2307462Notes

Reaction equation

HRID 2307462 reaction equation
[F:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[CH:4]=[CH:5][C:6]([OH:8])=O.[F:13][C:14]1[CH:19]=[CH:18][C:17]([N:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)=[CH:16][C:15]=1[CH:26]([NH2:28])[CH3:27].CCN=C=NCCCN(C)C.Cl.CCN(CC)CC>CN(C1C=CN=CC=1)C.C(Cl)Cl>[F:13][C:14]1[CH:19]=[CH:18][C:17]([N:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)=[CH:16][C:15]=1[CH:26]([NH:28][C:6](=[O:8])[CH:5]=[CH:4][C:3]1[CH:9]=[CH:10][CH:11]=[CH:12][C:2]=1[F:1])[CH3:27]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 679773-(2-Fluorophenyl)prop-2-enoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 22605573HCID 22605573, compound

Product 1

HCID 69919502(+/-)-N-[1-(2-Fluoro-5-morpholin-4-yl-phenyl)ethyl]-3-(2-fluoro-phenyl)acrylamide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-fluoro-cinnamic acid (83 mg), 1-(2-fluoro-5-morpholin-4-yl-phenyl)ethylamine, Preparation 25(112 mg), DMAP (61 mg), EDC.HCl (190 mg), and Et3N (202 mg) in CH2Cl2 (4 mL) was stirred for 16 hours. The crude product was purified by flash chromatography over silica gel (elution with 50% ethyl acetate in hexane) to give 150 mg of the title compound as a solid.

Workup

  1. customThe crude product was purified by flash chromatography over silica gel (elution with 50% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-16f11b881cbd47cca9ea992aadf5564e
Source dataset
uspto-grants-2004_12
Patent number
US06831080B2

Reaction notes

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