Triethylamine → N-[1-(3,4-Dihydro-2H-1,4-benzoxazin-6-yl)ethyl]-3-(2-fluorophenyl)-2-propenamide

HRID 2307465Notes

Reaction equation

HRID 2307465 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.[O:13]1[C:18]2[CH:19]=[CH:20][C:21]([CH:23]([NH2:25])[CH3:24])=[CH:22][C:17]=2[NH:16][CH2:15][CH2:14]1.CCN=C=NCCCN(C)C.Cl.C(N(CC)CC)C>CN(C1C=CN=CC=1)C.C(Cl)Cl>[O:13]1[C:18]2[CH:19]=[CH:20][C:21]([CH:23]([NH:25][C:6](=[O:8])[CH:5]=[CH:4][C:3]3[CH:9]=[CH:10][CH:11]=[CH:12][C:2]=3[F:1])[CH3:24])=[CH:22][C:17]=2[NH:16][CH2:15][CH2:14]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 679773-(2-Fluorophenyl)prop-2-enoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 22605500HCID 22605500, compound

Product 1

HCID 53411517N-[1-(3,4-Dihydro-2H-1,4-benzoxazin-6-yl)ethyl]-3-(2-fluorophenyl)-2-propenamide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-fluorocinnamic acid (0.5 mmol), (±)-1-(3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)ethylamine, Preparation 13 (28.5 mg, 0.16 mmol), EDC hydrochloride (192 mg, 1 mmol), DMAP (61 mg, 0.5 mmol), and triethylamine (202 mg, 2 mmol) in CH2Cl2 was stirred for 3 days. The reaction mixture was directly subjected to purification by flash column chromatography on silica using EtOAc/Hexane (8:1) to provide the desired product (149 mg).

Workup

  1. customThe reaction mixture was directly subjected to purification by flash column chromatography on silica

Sources & evidence

ORD record
ord-1d1d05be68884a49a6def9bc01fc9848
Source dataset
uspto-grants-2004_12
Patent number
US06831080B2

Reaction notes

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