Water → HCID 178420193, compound

HRID 1915002Notes

Reaction equation

HRID 1915002 reaction equation
[CH2:1]([C:8]1[CH:24]=[CH:23][C:11]2[NH:12][C:13]([CH:15](Cl)[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[N:14][C:10]=2[CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:25]1([C:31]2[N:36]=[CH:35][CH:34]=[CH:33][N:32]=2)[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1.C(N(CC)CC)C.O>CN(C=O)C>[CH2:1]([C:8]1[CH:24]=[CH:23][C:11]2[NH:12][C:13]([CH:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[N:28]3[CH2:29][CH2:30][N:25]([C:31]4[N:32]=[CH:33][CH:34]=[CH:35][N:36]=4)[CH2:26][CH2:27]3)=[N:14][C:10]=2[CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471Triethylamine2×HCID 887471-(2-Pyrimidinyl)piperazineHCID 178478432HCID 178478432, compound

Product 1

HCID 178420193HCID 178420193, compoundYield 86.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

300 mg of 5-benzyl-2-(chloro(phenyl)methyl)-1H-benzo[d]imidazole and 300 mg 2-(piperazin-1-yl)pyrimidine were dissolved in 5 ml of DMF at room temperature. After a few seconds, 0.5 ml of triethylamine was added, and the reaction mixture was stirred at room temperature, while being monitored by TLC. Once the starting material was no longer detected (overnight), additional 0.2 ml of triethylamine was added, followed by 3 ml of water, and the reaction mixture was cooled to 0° C. The precipitated solid was collected by vacuum filtration, washed with cold water and dried for 2 hours at 50° C., to give 360 mg (80% yield) of the product (BPRM-VR-2′ b).

Workup

  1. waitAfter a few seconds
  2. additionwas added
  3. temperaturethe reaction mixture was cooled to 0° C
  4. filtrationThe precipitated solid was collected by vacuum filtration
  5. washwashed with cold water
  6. customdried for 2 hours at 50° C.

Sources & evidence

ORD record
ord-09ba761c2cfd474d8dc3060e1af4b684
Source dataset
uspto-grants-2013_12
Patent number
US08614319B2

Reaction notes

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