Pyrrolidine → HCID 68665938, compound

HRID 1716850Notes

Reaction equation

HRID 1716850 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)[S:11][CH:12]=1>>[ClH:6].[N:1]1([CH2:7][C:8]2[N:9]=[C:10]([C:13]3[CH:28]=[CH:27][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:15][CH:14]=3)[S:11][CH:12]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 31268PyrrolidineHCID 57550208HCID 57550208, compound

Product 1

HCID 68665938HCID 68665938, compound

Procedure

Pyrrolidine (0.260 g, 3.66 mmol) was added to 1-{4-[4-(chloromethyl)-1,3-thiazol-2-yl]benzyl}-1H-benzimidazole (0.250 g, 0.737 mmol) at 5° C. and the mixture was allowed to stir for 1 h, allowed to warm to room temperature and evaporated to dryness in vacuo. The resultant residue was purified by flash chromatography (silica, CHCl3:MeOH 98:2) to afford the free amine of the title product. The purified material was stirred under HCl/ether and concentrated in vacuo to provide the title product, identified by NMR and mass spectral analyses. 1H NMR (300 MHz, DMSO-d6): 0.99 (br s, 1H), 9.61 (br s, 1H), 7.99 (s, 1H), 7.99 (d, 2H), 7.76-7.93 (m, 2H), 7.59 (d, 2H), 7.46-7.56 (m, 2H), 5.80 (s, 2H), 4.51 (d, 2H), 3.42-3.54 (m, 2H), 3.17 (s, 2H), 1.81-2.05 (m, 4H). LCMS (ESI+) 375.14 (MH+).

Workup

  1. customevaporated to dryness in vacuo
  2. customThe resultant residue was purified by flash chromatography (silica, CHCl3:MeOH 98:2)

Sources & evidence

ORD record
ord-fa210cf394fe4555b60cee4ce31a4e70
Source dataset
uspto-grants-2010_09
Patent number
US07803825B2

Reaction notes

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