Phenethylamine → 2-[(3-chloro-4-methoxybenzoyl)amino]-5-phenoxy-N-(2-phenylethyl)benzamide

HRID 2099976Notes

Reaction equation

HRID 2099976 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:24]=[CH:25][C:26]=1[O:27][CH3:28])[C:5]([NH:7][C:8]1[CH:16]=[CH:15][C:14]([O:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:13][C:9]=1[C:10]([OH:12])=O)=[O:6].C(N=C=NC(C)C)(C)C.C1C=CC2N(O)N=NC=2C=1.[CH2:48]([NH2:56])[CH2:49][C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:24]=[CH:25][C:26]=1[O:27][CH3:28])[C:5]([NH:7][C:8]1[CH:16]=[CH:15][C:14]([O:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:13][C:9]=1[C:10]([NH:56][CH2:48][CH2:49][C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)=[O:12])=[O:6]

Participants

6

Reactant 4

HCID 1001PhenethylamineHCID 12734DiisopropylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 577968992-(3-Chloro-4-methoxybenzamido)-5-phenoxybenzoic acid

Product 1

HCID 115696122-[(3-chloro-4-methoxybenzoyl)amino]-5-phenoxy-N-(2-phenylethyl)benzamideYield 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 43D (17 mg, 0.043 mmol) in DMF (1 mL) was treated with diisopropylcarbodiimide (6 mg, 0.047 mmol) and HOBt (12 mg, 0.086 mmol). The reaction was stirred for 1 hour at room temperature and then phenethylamine (104 mg, 0.86 mmol) was added. The resulting solution was stirred for 3 hours at room temperature, and then concentrated. The crude material was purified by chromatography (SiO2, 5% to 20% EtOAc in Hexanes) to afford 43E (16 mg, 75%). HPLC retention time=4.50 min (YMC S5 ODS 4.6×50 mm, 10-90% aqueous methanol containing 0.2% H3PO4, 4 min gradient, monitored at 220 nm)

Workup

  1. stirringThe resulting solution was stirred for 3 hours at room temperature
  2. concentrationconcentrated
  3. customThe crude material was purified by chromatography (SiO2, 5% to 20% EtOAc in Hexanes)

Sources & evidence

ORD record
ord-2d16015cf0fd4a6996ea3908b867fe0c
Source dataset
uspto-grants-2009_08
Patent number
US07569725B2

Reaction notes

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