Triethylamine → 2-(4-Chloro-phenyl)-cyclopropanecarboxylic acid[1-(2,3-dihydro-benzofuran-5-yl)-ethyl]-amide

HRID 857027Notes

Reaction equation

HRID 857027 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]([NH2:12])[CH3:11])=[CH:9][C:4]=2[CH2:3][CH2:2]1.[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([CH:20]2[CH2:22][CH:21]2[C:23](O)=[O:24])=[CH:16][CH:15]=1.CCN=C=NCCCN(C)C.Cl.C(N(CC)CC)C>CN(C1C=CN=CC=1)C.ClCCl>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]([NH:12][C:23]([CH:21]3[CH2:22][CH:20]3[C:17]3[CH:16]=[CH:15][C:14]([Cl:13])=[CH:19][CH:18]=3)=[O:24])[CH3:11])=[CH:9][C:4]=2[CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 2374122-(4-Chlorophenyl)cyclopropanecarboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 167684331-(2,3-Dihydro-1-benzofuran-5-yl)ethan-1-amine

Product 1

HCID 218646792-(4-Chloro-phenyl)-cyclopropanecarboxylic acid[1-(2,3-dihydro-benzofuran-5-yl)-ethyl]-amideYield 67.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-(2,3-dihydro-benzofuran-5-yl)-ethylamine (0.1 mmol), 2-(4-Chloro-phenyl)-cyclopropanecarboxylic acid (0.1 mmol), EDAC.HCl (0.2 mmol), DMAP (0.2 mmol), and triethylamine (0.4 mmol) in dichloromethane (2 mL) was stirred at room temperature overnight. The reaction mixture was purified by flash chromatography eluting with 50% hexanes in ethyl acetate to give the title compound (23 mg) as a solid.

Workup

  1. customThe reaction mixture was purified by flash chromatography
  2. washeluting with 50% hexanes in ethyl acetate

Sources & evidence

ORD record
ord-b6d9a95b08cf494c8c565a162455954c
Source dataset
uspto-grants-2006_12
Patent number
US07144881B2

Reaction notes

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