1,2-Dichloroethane → N-[5-bromo-3-methoxy-2-(2-methoxy-ethylamino)-phenyl]-4-isopropyl-benzamide

HRID 1661903Notes

Reaction equation

HRID 1661903 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([NH2:8])[C:5]([NH:9][CH2:10][CH2:11][O:12][CH3:13])=[C:4]([O:14][CH3:15])[CH:3]=1.C(Cl)CCl.[CH:20]([C:23]1[CH:31]=[CH:30][C:26]([C:27](O)=[O:28])=[CH:25][CH:24]=1)([CH3:22])[CH3:21].CCOC(C)=O>CN(C)C1C=CN=CC=1.ClCCl>[Br:1][C:2]1[CH:3]=[C:4]([O:14][CH3:15])[C:5]([NH:9][CH2:10][CH2:11][O:12][CH3:13])=[C:6]([NH:8][C:27](=[O:28])[C:26]2[CH:30]=[CH:31][C:23]([CH:20]([CH3:21])[CH3:22])=[CH:24][CH:25]=2)[CH:7]=1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 8857Ethyl AcetateHCID 108204-Isopropylbenzoic AcidHCID 577720825-bromo-3-methoxy-2-N-(2-methoxyethyl)benzene-1,2-diamine

Product 1

HCID 57771993N-[5-bromo-3-methoxy-2-(2-methoxy-ethylamino)-phenyl]-4-isopropyl-benzamideYield 98.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 4.95 g (18 mmol) 5-bromo-3-methoxy-N*2*-(2-methoxy-ethyl)-benzene-1,2-diamine, 5.15 g (27 mmol) EDC, 3.3 g (27 mmol) 4-dimethylamino-pyridine and 2.94 g (18 mmol) 4-isopropyl benzoic acid in 150 ml dichloromethane is stirred at room temperature for 14 h. After that 400 ml EtOAc are added and the organic phase washed with water (2×) and brine, dried over MgSO4, filtered and concentrated in vacuo. The residue is purified by flash-chromatography on silica gel (hexane:EtOAc=3:1) to afford 7.48 g of the title compound as a reddish oil.

Workup

  1. washthe organic phase washed with water (2×) and brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue is purified by flash-chromatography on silica gel (hexane:EtOAc=3:1)

Sources & evidence

ORD record
ord-b101d0aac73548dfa072a1016acdd708
Source dataset
uspto-grants-2011_10
Patent number
US08030497B2

Reaction notes

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