2-Chloro-1,1,1-triethoxyethane → HCID 89924058, compound

HRID 1500921Notes

Reaction equation

HRID 1500921 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[NH:9][CH:10]1[CH2:14][N:13]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)[C:12](=[O:24])[CH2:11]1.[Cl:25][CH2:26][C:27](OCC)(OCC)OCC>>[Cl:8][C:6]1[CH:5]=[CH:4][C:3]2[N:9]([CH:10]3[CH2:14][N:13]([CH2:15][C:16]4[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=4)[C:12](=[O:24])[CH2:11]3)[C:27]([CH2:26][Cl:25])=[N:1][C:2]=2[CH:7]=1

Participants

3

Reactant 2

HCID 3059222-Chloro-1,1,1-triethoxyethaneHCID 89923945HCID 89923945, compound

Product 1

HCID 89924058HCID 89924058, compound

Conditions

Temperature
80 °C

Procedure

A mixture of 4-[(2-amino-4-chlorophenyl)amino]-1-(4-methoxybenzyl)pyrrolidin-2-one (1.35 g, 3.91 mmol) and 2-chloro-1,1,1-triethoxyethane (10 mL) was stirred at 80° C. for 1 hour. The resulting mixture was concentrated in vacuo and the residue was purified by column chromatography (DCM: MeOH=20:1) to afford 4-[5-chloro-2-(chloromethyl)-1H-benzimidazol-1-yl]-1-(4-methoxybenzyl)pyrrolidin-2-one.

Workup

  1. concentrationThe resulting mixture was concentrated in vacuo
  2. customthe residue was purified by column chromatography (DCM: MeOH=20:1)

Sources & evidence

ORD record
ord-2452979e71964f2a9c66dcec56d237c5
Source dataset
uspto-grants-2015_12
Patent number
US09206191B2

Reaction notes

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