Oxalyl chloride → HCID 86588258, compound

HRID 1072538Notes

Reaction equation

HRID 1072538 reaction equation
[C:1](Cl)(=[O:5])[C:2](Cl)=O.[C:7]12(C(O)=O)[CH2:13][CH:10]([CH2:11][CH2:12]1)[CH2:9][CH2:8]2.NC1C=CC(C2[NH:25][C:26]3[CH:32]=[CH:31][C:30](N)=[CH:29][C:27]=3[N:28]=2)=CC=1>CN(C=O)C.N1C=CC=CC=1>[CH3:11][CH:12]([C:1]([C:2]1[NH:28][C:27]2[CH:29]=[CH:30][CH:31]=[CH:32][C:26]=2[N:25]=1)=[O:5])[CH2:7][CH2:8][CH2:9][CH2:10][CH3:13]

Participants

6

Reactant 3

HCID 65578Oxalyl chlorideHCID 140414Bicyclo(2.2.1)heptane-1-carboxylic acidHCID 178507432HCID 178507432, compound

Product 1

HCID 86588258HCID 86588258, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 1049PyridineSolvent

Conditions

Temperature
60 °C

Procedure

Bis-bicyclo[2:2:1]heptane-2-carbonyl benzimidazole was prepared as follows: oxalyl chloride (1.07 ml, 2 M in CH2Cl2) was added to bicyclo[2.2.1]heptane carboxylic acid (0.305 g, 2.14 mmole) followed by one drop DMF. The mixture was allowed to react at RT for 1.0 hour. To the above solution was added 2-(4-aminophenyl)-6-amino-benzimidazole (0.200 g, 0.89 mmole) in pyridine (2 ml). The reaction was heated to 60° C. overnight. The reaction was cooled and the precipitate filtered and washed with NaHCO3 and hexanes. The resulting solid was purified by preparative HPLC to give a solid that was 68% pure.

Workup

  1. customto react at RT for 1.0 hour
  2. temperatureThe reaction was cooled
  3. filtrationthe precipitate filtered
  4. washwashed with NaHCO3 and hexanes
  5. customThe resulting solid was purified by preparative HPLC
  6. customto give a solid

Sources & evidence

ORD record
ord-869083f57e934262953b0654a3539131
Source dataset
uspto-grants-2005_06
Patent number
US06911462B2

Reaction notes

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