1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → 2-(5-chloro-3-pyridyloxy)-N-(1-tert.butyldimethylsilyloxy-4-methylpent-2-yn-4-yl)butyramide

HRID 1374901Notes

Reaction equation

HRID 1374901 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([O:8][CH:9]([CH2:13][CH3:14])[C:10]([OH:12])=O)[CH:5]=[N:6][CH:7]=1.[NH2:15][C:16]([CH3:29])([CH3:28])[C:17]#[C:18][CH:19]([O:24][SiH:25]([CH3:27])[CH3:26])[C:20]([CH3:23])([CH3:22])[CH3:21].Cl.CN(CCCN=C=NCC)C>CN(C)C1C=CN=CC=1.ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([O:8][CH:9]([CH2:13][CH3:14])[C:10]([NH:15][C:16]([CH3:29])([CH3:28])[C:17]#[C:18][CH:19]([O:24][SiH:25]([CH3:27])[CH3:26])[C:20]([CH3:22])([CH3:23])[CH3:21])=[O:12])[CH:5]=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 210783782-(5-Chloro-3-pyridyloxy)butyric acidHCID 1317262094-Amino-1-tert.-butyldimethylsilyloxy-4-methylpent-2-yne

Product 1

HCID 1373300312-(5-chloro-3-pyridyloxy)-N-(1-tert.butyldimethylsilyloxy-4-methylpent-2-yn-4-yl)butyramide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

2-(5-Chloro-3-pyridyloxy)butyric acid (2.26 g), 4-amino-1-tert.-butyldimethylsilyloxy-4-methylpent-2-yne (2.27 g) and 4-dimethylaminopyridine (0.010 g) in dry dichloromethane (50 ml) were stirred at ambient temperature and N-dimethylaminopropyl-N′-ethylcarbodiimide hydrochloride (2.11 g) was added. The mixture was stirred at ambient temperature for 3 hours, stored for 18 hours, diluted with dichloromethane and washed with saturated aqueous sodium hydrogen carbonate (twice) then water (twice). The organic phase was dried over magnesium sulphate and evaporated under reduced pressure to give a dark yellow oil, 4.4 g, containing the required product.

Workup

  1. waitstored for 18 hours
  2. washwashed with saturated aqueous sodium hydrogen carbonate (twice) then water (twice)
  3. dry with materialThe organic phase was dried over magnesium sulphate
  4. customevaporated under reduced pressure
  5. customto give a dark yellow oil, 4.4 g

Sources & evidence

ORD record
ord-dd3742dad8f540248cdb344c651f97c1
Source dataset
uspto-grants-2007_01
Patent number
US07166621B2

Reaction notes

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