Oxalyl chloride → HCID 58970777, compound

HRID 1163074Notes

Reaction equation

HRID 1163074 reaction equation
[C:1]1([C:7]2[N:11]([CH2:12][C:13]3[CH:21]=[CH:20][C:16]([C:17](O)=[O:18])=[CH:15][CH:14]=3)[C:10]3[CH:22]=[CH:23][CH:24]=[CH:25][C:9]=3[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Cl)(=O)C(Cl)=O.[NH:32]1[CH2:36][CH2:35][CH:34]([OH:37])[CH2:33]1>C(Cl)Cl.CN(C=O)C>[C:1]1([C:7]2[N:11]([CH2:12][C:13]3[CH:21]=[CH:20][C:16]([C:17]([N:32]4[CH2:36][CH2:35][CH:34]([OH:37])[CH2:33]4)=[O:18])=[CH:15][CH:14]=3)[C:10]3[CH:22]=[CH:23][CH:24]=[CH:25][C:9]=3[N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 65578Oxalyl chlorideHCID 982104-HydroxypyrrolidineHCID 58970773HCID 58970773, compound

Product 1

HCID 58970777HCID 58970777, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 4-(2-phenyl-benzoimidazol-1-ylmethyl)-benzoic acid (1 g, 3 mmol) in DCM is treated with 2 drops of DMF followed by oxalylchloride (3 mL, 6 mmol, 2M solution in DCM), stirred at room temperature for 2 hours and concentrated in vacuo. The resultant residue is dissolved in DCM, treated with 3-pyrrolidinol (0.3 mL, 3.6 mmol), stirred at room temperature for 8 hours then concentrated to give 1-{4-[(2-phenyl-1H-benzimidazol-1-yl)methyl]benzoyl}pyrrolidin-3-ol identified by HPLC and MS [398.4 m/e (M+H)].

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe resultant residue is dissolved in DCM
  3. stirringstirred at room temperature for 8 hours
  4. concentrationthen concentrated

Sources & evidence

ORD record
ord-74a149deab9e4ff2876d3448ab6f14ef
Source dataset
uspto-grants-2010_10
Patent number
US07820825B2

Reaction notes

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