1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → 2-(5-chloro-3-pyridyloxy)-N-(2-methylpent-3-yn-2-yl)butyramide

HRID 1374890Notes

Reaction equation

HRID 1374890 reaction equation
Cl.N[CH2:3][CH:4]([CH3:8])[C:5]#[C:6][CH3:7].O.O[N:11]1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[Cl:32][C:33]1[CH:34]=[C:35]([O:39][CH:40]([CH2:44][CH3:45])[C:41](O)=[O:42])[CH:36]=[N:37][CH:38]=1>CN(C)C=O.O.C(N(CC)CC)C>[Cl:32][C:33]1[CH:34]=[C:35]([O:39][CH:40]([CH2:44][CH3:45])[C:41]([NH:11][C:4]([CH3:3])([C:5]#[C:6][CH3:7])[CH3:8])=[O:42])[CH:36]=[N:37][CH:38]=1

Participants

8

Reactant 4

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 210783782-(5-Chloro-3-pyridyloxy)butyric acidHCID 210784214-Aminomethyl-pent-2-yne hydrochloride

Product 1

HCID 210783862-(5-chloro-3-pyridyloxy)-N-(2-methylpent-3-yn-2-yl)butyramide

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

To a stirred solution of 4-aminomethyl-pent-2-yne hydrochloride (2.67 g; prepared as described below) in dry N,N-dimethyl formamide (150 ml) at ambient temperature was added dry triethylamine (4.2 ml). The mixture was stirred at ambient temperature for 5 minutes and 1-hydroxybenzotriazole hydrate (2.97 g), N-(3-dimethylaminopropyl)-N′-ethyl carbodiimide hydrochloride (4.22 g) and 2-(5-chloro-3-pyridyloxy)butyric acid (4.53 g) were added sequentially. The mixture was stirred at ambient temperature for 2.75 hours, stored at ambient temperature for 18 hour and poured into water. The product was extracted into diethyl ether (three times) and the extracts were combined, washed with aqueous sodium o hydrogen carbonate (twice), water (twice) and dried over magnesium sulphate. The solvent was evaporated under reduced pressure and the residual gum fractionated by chromatography (silica: diethyl ether) to give a pale yellow oil, which was triturated with hexane to give the required product as a colourless solid, 4.5 g, m.p. 87–89° C.

Workup

  1. stirringThe mixture was stirred at ambient temperature for 2.75 hours
  2. waitstored at ambient temperature for 18 hour
  3. extractionThe product was extracted into diethyl ether (three times)
  4. washwashed with aqueous sodium o hydrogen carbonate (twice), water (twice) and
  5. dry with materialdried over magnesium sulphate
  6. customThe solvent was evaporated under reduced pressure
  7. customto give a pale yellow oil, which
  8. customwas triturated with hexane

Sources & evidence

ORD record
ord-ba3fb807c5c84802af8f07162190c794
Source dataset
uspto-grants-2007_01
Patent number
US07166621B2

Reaction notes

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