Pyrrolidine → HCID 59457512, compound

HRID 1710742Notes

Reaction equation

HRID 1710742 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[O:13][CH:14]=[C:15]([CH2:17][C:18]([OH:20])=O)[N:16]=2)=[CH:8][CH:7]=1.ON1C2C=[CH:28][CH:29]=[CH:30][C:25]=2[N:24]=N1.Cl.CN(C)CCCN=C=NCC.N1CCCC1>ClCCl.O>[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]2[O:13][CH:14]=[C:15]([CH2:17][C:18](=[O:20])[N:24]3[CH2:25][CH2:30][CH2:29][CH2:28]3)[N:16]=2)=[CH:10][CH:11]=1

Participants

7

Reactant 4

HCID 31268PyrrolidineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 59457517HCID 59457517, compound

Product 1

HCID 59457512HCID 59457512, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of {2-[4-(3-chloropropoxy)phenyl]-1,3-oxazol-4-yl}acetic acid ax63 (0.5 g, 1.69 mmol, 1 eq) in dichloromethane (50 ml) is added 1-hydroxybenzotriazole (0.025 g, 0.19 mmol, 0.11 eq) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.357 g, 1.86 mmol, 1.1 eq). To that solution is added pyrrolidine (0.29 ml, 3.38 mmol, 2 eq) and the mixture is stirred at room temperature overnight. The mixture is poured into water and extracted with dichloromethane. The organic layer is dried over magnesium sulfate and the solvent is removed under vacuum to afford 0.51 g of 2-[4-(3-chloropropoxy)phenyl]-4-(2-oxo-2-pyrrolidin-1-ylethyl)-1,3-oxazole ax64 as a pale yellow oil.

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialThe organic layer is dried over magnesium sulfate
  3. customthe solvent is removed under vacuum

Sources & evidence

ORD record
ord-71ea83e0d52c4809943617baafc016f7
Source dataset
uspto-grants-2010_09
Patent number
US07790720B2

Reaction notes

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