1-Iodo-4-{[1-methoxy-3-(methylamino)-1,3-dioxopropan-2-yl](methyl)carbamoyl}benzene → 1-[1-(Cyclopropylamino)ethyl]-4-[(4-{[1-methoxy-3-(methylamino)-1,3-dioxopropan-2-yl](methyl)carbamoyl}phenyl)ethynyl]benzene

HRID 1519699Notes

Reaction equation

HRID 1519699 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:20])[N:9]([CH:11]([C:16]([NH:18][CH3:19])=[O:17])[C:12]([O:14][CH3:15])=[O:13])[CH3:10])=[CH:4][CH:3]=1.[C:21]([C:23]1[CH:28]=[CH:27][C:26]([CH:29]([NH:31][CH:32]2[CH2:34][CH2:33]2)[CH3:30])=[CH:25][CH:24]=1)#[CH:22]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I.C(Cl)(Cl)Cl>[CH:32]1([NH:31][CH:29]([C:26]2[CH:25]=[CH:24][C:23]([C:21]#[C:22][C:2]3[CH:7]=[CH:6][C:5]([C:8](=[O:20])[N:9]([CH:11]([C:16]([NH:18][CH3:19])=[O:17])[C:12]([O:14][CH3:15])=[O:13])[CH3:10])=[CH:4][CH:3]=3)=[CH:28][CH:27]=2)[CH3:30])[CH2:34][CH2:33]1

Participants

6

Reactant 2

HCID 712681491-Iodo-4-{[1-methoxy-3-(methylamino)-1,3-dioxopropan-2-yl](methyl)carbamoyl}benzeneHCID 86679268N-[1-(4-ethynylphenyl)ethyl]cyclopropylamine

Product 1

HCID 712681761-[1-(Cyclopropylamino)ethyl]-4-[(4-{[1-methoxy-3-(methylamino)-1,3-dioxopropan-2-yl](methyl)carbamoyl}phenyl)ethynyl]benzeneYield 85%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6212ChloroformSolvent

Procedure

Intermediate 6-2 (0.11 g), PdCl2(PPh3)2 (10 mg), CuI (5.0 mg), and TEA (28 mg) were added to a chloroform (5.0 mL) solution of N-[1-(4-ethynylphenyl)ethyl]cyclopropylamine (51 mg) as obtained in Example 14-(3), and the mixture was stirred in a nitrogen atmosphere for 2 hours at room temperature, whereafter the reaction mixture was concentrated. The resulting residue was purified by OH type silica gel chromatography (ethyl acetate) to obtain 1-[1-(cyclopropylamino)ethyl]-4-[(4-{[1-methoxy-3-(methylamino)-1,3-dioxopropan-2-yl](methyl)carbamoyl}phenyl)ethynyl]benzene (light yellow foam) (0.10 g, 85%).

Workup

  1. concentrationwas concentrated
  2. customThe resulting residue was purified by OH type silica gel chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-cdd4588863c64e8aa71cbe0fc105875b
Source dataset
uspto-grants-2015_07
Patent number
US09073821B2

Reaction notes

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