1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → 2-(6-quinolinyloxy)-N-(1-tert-butyldimethylsilyloxy-4-methylpent-2-yn-4-yl)butyramide

HRID 1244804Notes

Reaction equation

HRID 1244804 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([O:11][CH:12]([CH2:16][CH3:17])[C:13]([OH:15])=O)=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[NH2:18][C:19]([CH3:32])([CH3:31])[C:20]#[C:21][CH2:22][O:23][Si:24]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25].Cl.CN(C)CCCN=C=NCC.CCCCCC.C(OCC)(=O)C>CN(C)C1C=CN=CC=1.ClCCl>[N:1]1[C:10]2[C:5](=[CH:6][C:7]([O:11][CH:12]([CH2:16][CH3:17])[C:13]([NH:18][C:19]([CH3:32])([CH3:31])[C:20]#[C:21][CH2:22][O:23][Si:24]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:25])[CH3:26])=[O:15])=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 21226206Ethyl acetate hexaneHCID 219231162-(6-Quinolinyloxy)butyric acidHCID 219231344-Amino-1-tert-butyldimethylsilyloxy-4-methylpent-2-yne

Product 1

HCID 219231372-(6-quinolinyloxy)-N-(1-tert-butyldimethylsilyloxy-4-methylpent-2-yn-4-yl)butyramideYield 10.9%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

2-(6-Quinolinyloxy)butyric acid (0.61 g), 4-amino-1-tert-butyldimethylsilyloxy-4-methylpent-2-yne (0.57 g) and 4-dimethylaminopyridine (0.010 g) in dry dichloromethane (10 ml) were stirred and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (0.53 g) was added. The mixture was stirred at ambient temperature for 3.5 hours, stored for 2 days, diluted with dichloromethane, washed with saturated aqueous sodium hydrogen carbonate (twice) and then with water. The organic phase was dried over magnesium sulphate and evaporated under reduced pressure to give a yellow oil. The oil was fractionated by chromatography (silica; hexane/ethyl acetate, 3:1 by volume) to give a gum that was triturated with hexane to give the required product (0.12 g) as a colourless solid, m.p. 78–80° C.

Workup

  1. waitstored for 2 days
  2. washwashed with saturated aqueous sodium hydrogen carbonate (twice) and then with water
  3. dry with materialThe organic phase was dried over magnesium sulphate
  4. customevaporated under reduced pressure
  5. customto give a yellow oil
  6. customto give a gum that
  7. customwas triturated with hexane

Sources & evidence

ORD record
ord-3839cb092e7449049e20618601ebb118
Source dataset
uspto-grants-2006_10
Patent number
US07122672B2

Reaction notes

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