Oxalyl chloride → HCID 25032264, compound

HRID 1163071Notes

Reaction equation

HRID 1163071 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.C(N(C(C)C)CC)(C)C.[CH3:41][N:42]([CH3:48])[CH:43]1[CH2:47][CH2:46][NH:45][CH2:44]1>C(Cl)Cl.CN(C=O)C>[CH3:41][N:42]([CH:43]1[CH2:47][CH2:46][N:45]([C:17](=[O:18])[C:16]2[CH:15]=[CH:14][C:13]([CH2:12][N:11]3[C:10]4[CH:22]=[CH:23][CH:24]=[CH:25][C:9]=4[N:8]=[C:7]3[C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[CH:21][CH:20]=2)[CH2:44]1)[CH3:48]

Participants

7

Reactant 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 27585193-(Dimethylamino)pyrrolidineHCID 58970773HCID 58970773, compound

Product 1

HCID 25032264HCID 25032264, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

The 4-(2-phenyl-benzoimidazol-1-ylmethyl)-benzoic acid (0.2 mmol) obtained in step 2 is dissolved in DCM (5 mL) and oxalylchloride (0.2 mL, 0.4 mmol, 2 M solution in DCM) and DMF (2 drops) are added. The solution is stirred for 2 hours at room temperature then concentrated in vacuo. The residue is dissolved in THF, treated with diisopropylethylamine (DIEA) (0.09 mL, 0.5 mmol) and 3-(dimethylamino)pyrrolidine (0.22 mmol, 22 uL), stirred at room temperature overnight then concentrated. This residue is dissolved in a mixture of DMSO, MeOH and water (1.5 mL) and purified by reverse-phase semi-preparative HPLC1 to the title product as a white powder (13 mg), identified by HPLC2 and MS [425.2 m/e (M+H)].

Workup

  1. concentrationthen concentrated in vacuo
  2. dissolutionThe residue is dissolved in THF
  3. stirringstirred at room temperature overnight
  4. concentrationthen concentrated
  5. dissolutionThis residue is dissolved in a mixture of DMSO, MeOH and water (1.5 mL)
  6. custompurified by reverse-phase semi-preparative HPLC1 to the title product as a white powder (13 mg)

Sources & evidence

ORD record
ord-094c54ae3454423e82fe5176359422b3
Source dataset
uspto-grants-2010_10
Patent number
US07820825B2

Reaction notes

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