HCID 178480615, compound → HCID 178480614, compound

HRID 2243365Notes

Reaction equation

HRID 2243365 reaction equation
[F:1][C:2]1[C:25]([N:26]2[CH2:31][CH2:30][N:29]([CH3:32])[CH2:28][CH2:27]2)=[CH:24][C:5]2[NH:6][C:7]([C:9]3[C:21]4[C:20]5[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=5)[C:14](=[N:22]O)[C:13]=4[CH:12]=[CH:11][CH:10]=3)=[N:8][C:4]=2[CH:3]=1>[Ni].C(O)C.O1CCCC1>[F:1][C:2]1[C:25]([N:26]2[CH2:31][CH2:30][N:29]([CH3:32])[CH2:28][CH2:27]2)=[CH:24][C:5]2[NH:6][C:7]([C:9]3[C:21]4[C:20]5[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=5)[CH:14]([NH2:22])[C:13]=4[CH:12]=[CH:11][CH:10]=3)=[N:8][C:4]=2[CH:3]=1

Participants

5

Reactant 1

HCID 178480615HCID 178480615, compound

Product 1

HCID 178480614HCID 178480614, compoundYield 90.1%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

The procedure used in Example 6 is followed, starting from 1.95 g of 4-[5-fluoro-6-(4-methylpiperazin-1-yl)-1H-benzimidazol-2-yl]-9H-fluoren-9-one oxime (Z,E), obtained in the previous stage, and 285 mg of Raney nickel in 40 ml of ethanol and 40 ml of tetrahydrofuran for 16 hours at 60° C. under an initial hydrogen pressure of one bar. After filtration of the catalyst, concentration to dryness under reduced pressure and purification by formation of a paste with diisopropyl ether, in this way we obtain 1.7 g of 4-[5-fluoro-6-(4-methylpiperazin-1-yl)-1H-benzimidazol-2-yl]-9H-fluoren-9(R,S)-ylamine, in the form of an orange powder, which is used as it is in the following stage, with the following characteristics:

Workup

  1. filtrationAfter filtration of the catalyst, concentration to dryness
  2. customunder reduced pressure and purification by formation of a paste with diisopropyl ether

Sources & evidence

ORD record
ord-8724bc6538184b9383a2c363614e6993
Source dataset
uspto-grants-2010_03
Patent number
US07674795B2

Reaction notes

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