1,1'-Carbonyldiimidazole → HCID 22632892, compound

HRID 2270217Notes

Reaction equation

HRID 2270217 reaction equation
[CH2:1]([O:8][NH:9][C:10]([C:12]1[C:13]([NH:26][CH:27]2[CH2:29][CH2:28]2)=[N:14][C:15]([N:19]2[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]2)=[C:16]([F:18])[CH:17]=1)=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1N=CN([C:35](N2C=NC=C2)=[O:36])C=1>C(Cl)(Cl)Cl.CO.ClCCl>[CH2:1]([O:8][N:9]1[C:10](=[O:11])[C:12]2[CH:17]=[C:16]([F:18])[C:15]([N:19]3[CH2:20][CH2:21][N:22]([CH3:25])[CH2:23][CH2:24]3)=[N:14][C:13]=2[N:26]([CH:27]2[CH2:29][CH2:28]2)[C:35]1=[O:36])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 22632922HCID 22632922, compound

Product 1

HCID 22632892HCID 22632892, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

Following the procedure of Example K-2, the reaction of N-benzyloxy-2-cyclopropylamino-5-fluoro-6-(4-methylpiperazinyl)-3-pyridinecarboxamide (Example J-2, 160 mg, 0.42 mmol) with CDI (135 mg, 0.83 mmol) in chloroform (2 mL) and purification of the reaction mixture by flash chromatography on a silica gel with 5% of MeOH/dichloromethane as eluent provided 125 mg of the title compound as powder, mp 188-189° C.

Sources & evidence

ORD record
ord-ff161d80093c40439f0dc3db34e92539
Source dataset
uspto-grants-2001_12
Patent number
US06331538B1

Reaction notes

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