HCID 178480419, compound → HCID 178480418, compound

HRID 2243358Notes

Reaction equation

HRID 2243358 reaction equation
[F:1][C:2]1[C:25]([N:26]2[CH2:32][CH2:31][CH2:30][N:29]([CH3:33])[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[CH2:32][CH2:31][CH2:30][N:29]([CH3:33])[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 178480419HCID 178480419, compound

Product 1

HCID 178480418HCID 178480418, compoundYield 76.1%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

The procedure used in Example 6 is followed, starting from 950 mg of 4-[5-fluoro-6-(4-methylperhydro-1,4-diazepin-1-yl)-1H-benzimidazol-2-yl]-9H-fluoren-9-one oxime (Z,E), obtained in the previous stage, and 135 mg of Raney nickel in 20 ml of ethanol and 20 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 then purification by formation of a paste with diisopropyl ether, in this way we obtain 700 mg of 4-[5-fluoro-6-(4-methylperhydro-1,4-diazepin-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.

Workup

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

Sources & evidence

ORD record
ord-14dfbf2f85f04089bd0752445645ec11
Source dataset
uspto-grants-2010_03
Patent number
US07674795B2

Reaction notes

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