HCID 19937308, compound → 2-amino-3-(4-chlorophenyl)-N-(2,2-diethoxyethyl)-N-isopropylpropionamide

HRID 1994403Notes

Reaction equation

HRID 1994403 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9](C)[C:10]([N:12]([CH2:16][CH:17]([O:21][CH2:22][CH3:23])[O:18][CH2:19][CH3:20])[CH:13]([CH3:15])[CH3:14])=[O:11])=[CH:4][CH:3]=1.C([NH:27]CC)C.C(Cl)Cl>>[NH2:27][CH:9]([CH2:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)[C:10]([N:12]([CH2:16][CH:17]([O:21][CH2:22][CH3:23])[O:18][CH2:19][CH3:20])[CH:13]([CH3:15])[CH3:14])=[O:11]

Participants

3

Reactant 2

HCID 19937308HCID 19937308, compoundHCID 673398213-(4-chlorophenyl)-N-(2,2-diethoxyethyl)-N-isopropyl-2-methylpropionamide

Product 1

HCID 673416462-amino-3-(4-chlorophenyl)-N-(2,2-diethoxyethyl)-N-isopropylpropionamide

Procedure

A solution of 530 mg (0.915 mmol) of 3-(4-chlorophenyl)-N-(2,2-diethoxyethyl)-N-isopropyl-2-methylpropionamide in 15 ml of a 20% diethylamine DCM solution is stirred at room temperature overnight. The reaction mixture is concentrated in vacuo and purified by chromatography on 5 g of SiO2 (eluent DCM followed by 20% EtOAc/DCM followed by 20% MeOH/DCM). 320 mg of the desired product are obtained as an oil. MW=356.19 (calculated, monoisotopic); measured value (M+H)+=357

Workup

  1. concentrationThe reaction mixture is concentrated in vacuo
  2. custompurified by chromatography on 5 g of SiO2 (eluent DCM followed by 20% EtOAc/DCM followed by 20% MeOH/DCM)

Sources & evidence

ORD record
ord-2e6c93aa361c4464be693a0d4af3b763
Source dataset
uspto-grants-2010_01
Patent number
US07652007B2

Reaction notes

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