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

HRID 2307459Notes

Reaction equation

HRID 2307459 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]([F:30])([F:29])[CH:15]([NH2:28])[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([N:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)[CH:17]=1.CCN=C=NCCCN(C)C.Cl.CCN(CC)CC>CN(C1C=CN=CC=1)C.C(Cl)Cl>[F:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[CH:4]=[CH:5][C:6]([NH:28][CH:15]([C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([N:22]2[CH2:23][CH2:24][O:25][CH2:26][CH2:27]2)[CH:17]=1)[C:14]([F:13])([F:30])[F:29])=[O:8]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 679773-(2-Fluorophenyl)prop-2-enoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 22605494HCID 22605494, compound

Product 1

HCID 69918775(+/-)-3-(2-fluoro-phenyl)-N-[2,2,2-trifluoro-1-(3-morpholin-4-yl-phenyl)ethyl]acrylamide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-fluorocinnamic acid (33 mg), 2,2,2-trifluoro-1-(3-morpholin-4-yl-phenyl)-ethylamine, Preparation 23 (52 mg), DMAP (24 mg), EDC.HCl (80 mg), and Et3N (80 mg) in CH2Cl2 (4 mL) was stirred for 16 hours. Purification by flash chromatography over silica gel (elution with 50% ethyl acetate in hexane) gave 65 mg of the title compound as a solid.

Workup

  1. customPurification by flash chromatography over silica gel (elution with 50% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-1b59bbd644ea45d0b39c70a6eabe3227
Source dataset
uspto-grants-2004_12
Patent number
US06831080B2

Reaction notes

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