Pyrrolidine → HCID 68665582, compound

HRID 1716828Notes

Reaction equation

HRID 1716828 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:6][CH2:7][C:8]1[N:9]=[C:10]([C:13]2[CH:28]=[CH:27][C:16]([CH2:17][N:18]3[C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=4[N:20]=[CH:19]3)=[CH:15][CH:14]=2)[O:11][CH:12]=1>>[ClH:6].[N:1]1([CH2:7][C:8]2[N:9]=[C:10]([C:13]3[CH:14]=[CH:15][C:16]([CH2:17][N:18]4[C:22]5[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=5[N:20]=[CH:19]4)=[CH:27][CH:28]=3)[O:11][CH:12]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 31268PyrrolidineHCID 57550195HCID 57550195, compound

Product 1

HCID 68665582HCID 68665582, compoundYield 51%

Procedure

A mixture of pyrrolidine (0.032 g, 0.46 mmol) and 1-[4-(4-chloromethyl-oxazol-2-yl)-benzyl]-1H-benzoimidazole (0.05 g, 0.15 mmol) in a sealed tube at room temperature was stirred for 30 minutes. The tube was unsealed and the reaction mixture was concentrated in vacuo to remove the excess pyrrolidine. The residue was purified by column chromatography (silica, CHCl3/CH3OH 4%). The purified free base was treated with methanolic HCl solution, stirred for several minutes at room temperature and evaporated to dryness to afford the title product as a white solid in 51% yield, identified by NMR and mass spectral analyses. 1H NMR (300 MHz, DMSO-d6): 9.35 (s, 1H); 8.33 (s, 1H); 8.00 (d, 2H); 7.85 (m, 1H); 7.74 (m, 1H); 7.59 (d, 2H); 7.49 (m, 2H); 5.79 (s, 2H); 4.35 (s, 2H); 3.36 (m br, 4H); 1.98 (m, 4H)). LCMS (ESI+) 359 (MH+).

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. customto remove the excess pyrrolidine
  3. customThe residue was purified by column chromatography (silica, CHCl3/CH3OH 4%)
  4. additionThe purified free base was treated with methanolic HCl solution
  5. stirringstirred for several minutes at room temperature
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-0ba8521d68e1437eb306a214a383543f
Source dataset
uspto-grants-2010_09
Patent number
US07803825B2

Reaction notes

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