Water → HCID 178420368, compound

HRID 2243306Notes

Reaction equation

Cl.Cl.[CH2:3]([NH:10][NH2:11])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C([O-])(=O)C.[Na+].O.[N:18]1[C:26]2[CH:25]=[CH:24][N:23]=[CH:22][C:21]=2[NH:20][C:19]=1[C:27]1[C:39]2[C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[C:32](=O)[C:31]=2[CH:30]=[CH:29][CH:28]=1>CO>[CH2:3]([NH:10][N:11]=[C:32]1[C:31]2[CH:30]=[CH:29][CH:28]=[C:27]([C:19]3[NH:18][C:26]4[CH:25]=[CH:24][N:23]=[CH:22][C:21]=4[N:20]=3)[C:39]=2[C:38]2[C:33]1=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

Conditions

Temperature: 52.5 °C

Procedure

In a 10-ml round-bottomed flask, dissolve 100 mg of 4-(3H-imidazo[4,5-c]pyridin-2-yl)-fluoren-9-one, obtained in Example 1, in 3 ml of methanol, then add successively 197 mg of benzylhydrazine dihydrochloride and 138 mg of dry sodium acetate and heat at 50-55° C. for 5 hours. Pour the cooled reaction mixture into 10 ml of water, extract with ethyl acetate then twice with dichloromethane. Combine the organic phases, wash with a saturated aqueous solution of sodium chloride, dry over sodium sulphate then concentrate under reduced pressure. After purification by chromatography on silica gel (40-63 μm), eluting with a mixture of dichloromethane and methanol (93-7 by volume), we obtain 37 mg of N-benzyl-N′-[4-(1H-imidazo[4,5-c]pyridin-2-yl)-fluoren-9-ylidene]-hydrazine, in the form of a yellow foam with the following characteristics:

Workup

additionPour
extractionextract with ethyl acetate
washwash with a saturated aqueous solution of sodium chloride
dry with materialdry over sodium sulphate
concentrationthen concentrate under reduced pressure
customAfter purification by chromatography on silica gel (40-63 μm)
washeluting with a mixture of dichloromethane and methanol (93-7 by volume), we

Sources & evidence

ORD record: ord-cca003ae25394723b105f1054ba6c2a3
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07674795B2

Reaction notes

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