Imidazole → HCID 22346333, compound

HRID 897277Notes

Reaction equation

HRID 897277 reaction equation
Cl[C:2]1[N:11]=[C:10]([C:12]([NH:14][CH2:15][C:16]2[CH:21]=[C:20]([Cl:22])[CH:19]=[C:18]([Cl:23])[CH:17]=2)=[O:13])[C:9]([OH:24])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[NH:25]1[CH:29]=[CH:28][N:27]=[CH:26]1>CN(C=O)C>[Cl:23][C:18]1[CH:17]=[C:16]([CH:21]=[C:20]([Cl:22])[CH:19]=1)[CH2:15][NH:14][C:12]([C:10]1[C:9]([OH:24])=[C:8]2[C:3]([CH:4]=[CH:5][CH:6]=[N:7]2)=[C:2]([N:25]2[CH:29]=[CH:28][N:27]=[CH:26]2)[N:11]=1)=[O:13]

Participants

4

Reactant 2

HCID 795ImidazoleHCID 10271271HCID 10271271, compound

Product 1

HCID 22346333HCID 22346333, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The chloride from Example 44 Step 5 (8.0 mg, 0.021 mmol) and imidazole (80 mg) were fused at 160 C for 1 hr under argon. The residue was dissolved in DMF (0.5 ml) and purified by preparative HPLC. (Gilson semi preparative HPLC system and a YMC Combiprep Pro Column (50×20 mm I.D., C18, S-5 um, 120A) eluting with 5-95% acetonitrile/water (0.1% TFA) at 15 ml/min) to afford the title compound after lyophilization.

Workup

  1. custompurified by preparative HPLC
  2. wash(Gilson semi preparative HPLC system and a YMC Combiprep Pro Column (50×20 mm I.D., C18, S-5 um, 120A) eluting with 5-95% acetonitrile/water (0.1% TFA) at 15 ml/min)

Sources & evidence

ORD record
ord-79473bcc4f944fd6bf78fe778a4493a6
Source dataset
uspto-grants-2005_07
Patent number
US06921759B2

Reaction notes

Loading…