Carbonate Ion → 5-Chloro-1-{2-oxo-1-phenyl-2-[3-(4-propylpiperazin-1-yl)pyrrolidin-1-yl]-ethyl}-1,3-dihydrobenzimidazol-2-one

HRID 1631970Notes

Reaction equation

HRID 1631970 reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][C:5]2[N:6]([CH:10]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:11](O)=[O:12])[C:7](=[O:9])[NH:8][C:4]=2[CH:3]=1.C1C=CC2N(O)N=NC=2C=1.N=C=N.[CH2:35]([N:38]1[CH2:43][CH2:42][N:41]([CH:44]2[CH2:48][CH2:47][NH:46][CH2:45]2)[CH2:40][CH2:39]1)[CH2:36][CH3:37].C(=O)([O-])[O-]>ClCCl>[Cl:1][C:2]1[CH:21]=[CH:20][C:5]2[N:6]([CH:10]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:11](=[O:12])[N:46]3[CH2:47][CH2:48][CH:44]([N:41]4[CH2:42][CH2:43][N:38]([CH2:35][CH2:36][CH3:37])[CH2:39][CH2:40]4)[CH2:45]3)[C:7](=[O:9])[NH:8][C:4]=2[CH:3]=1

Participants

7

Reactant 5

HCID 19660Carbonate IonHCID 757711-HydroxybenzotriazoleHCID 160435CarbodiimideHCID 24901021(5-Chloro-2-oxo-2,3-dihydrobenzimidazol-1-yl)phenyl-acetic acidHCID 667546611-Propyl-4-pyrrolidin-3-ylpiperazine

Product 1

HCID 667550625-Chloro-1-{2-oxo-1-phenyl-2-[3-(4-propylpiperazin-1-yl)pyrrolidin-1-yl]-ethyl}-1,3-dihydrobenzimidazol-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

110 mg (0.36 mmol) of (5-chloro-2-oxo-2,3-dihydrobenzimidazol-1-yl)phenyl-acetic acid (VIIIe), 69.1 mg (0.51 mmol) of HOBt and 335 mg (0.44 mmol, 1.3 mmol/g) of solid phase-bound PS-carbodiimide were dissolved in 6 ml of dry dichloromethane in a screw-cap tube and shaken mechanically at room temperature for 10 min. 78.9 mg (0.40 mmol) of 1-propyl-4-pyrrolidin-3-ylpiperazine were added, and the mixture was then shaken mechanically overnight. Three equivalents of solid phase-bound MP-carbonate were then added to the reaction mixture, and shaking was continued for 2 h. The solid phase-bound reagents were filtered off and washed with dichloromethane. The filtrate was concentrated in vacuo and the residue was dried in vacuo. The reaction product was used without further purification for the next reaction step.

Workup

  1. stirringthe mixture was then shaken mechanically overnight
  2. stirringshaking
  3. waitwas continued for 2 h
  4. filtrationThe solid phase-bound reagents were filtered off
  5. washwashed with dichloromethane
  6. concentrationThe filtrate was concentrated in vacuo
  7. customthe residue was dried in vacuo
  8. customThe reaction product was used without further purification for the next reaction step

Sources & evidence

ORD record
ord-6331ca7fba4245008f2aa8cf14bcc43a
Source dataset
uspto-grants-2014_07
Patent number
US08791148B2

Reaction notes

Loading…