HCID 137227841, compound → HCID 131727952, compound

HRID 2243348Notes

Reaction equation

HRID 2243348 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[C:17]1[CH:29]=[C:28]([NH:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH:27]=[C:26]2[C:18]=1[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:24]=1[C:25]2=[N:38]O)=[O:7])([CH3:4])([CH3:3])[CH3:2]>[Ni].C(O)C.O1CCCC1>[C:1]([O:5][C:6]([N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[C:17]1[CH:29]=[C:28]([NH:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH:27]=[C:26]2[C:18]=1[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:24]=1[CH:25]2[NH2:38])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 1

HCID 137227841HCID 137227841, compound

Product 1

HCID 131727952HCID 131727952, compoundYield 102.7%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

The procedure used in Example 6 is followed, but starting from 250 mg of 5-[1-(tert-butoxycarbonyl)benzimidazol-2-yl]-7-( tert-butoxycarbonyl-amino)-9H-fluoren-9-one oxime (Z,E), obtained in the previous stage, and 29 mg of Raney nickel in 4 ml of ethanol and 4 ml of tetrahydrofuran for 10 hours at 60° C. under an initial hydrogen pressure of one bar. After filtration of the catalyst, and purification by formation of a paste in diisopropyl ether, in this way we obtain 250 mg of 5-[1-(tert-butoxycarbonyl)benzimidazol-2-yl]-7-(tert-butoxycarbonylamino)-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, and purification by formation of a paste in diisopropyl ether

Sources & evidence

ORD record
ord-f06a3f661a8d4f92b78c5be2cc7956fd
Source dataset
uspto-grants-2010_03
Patent number
US07674795B2

Reaction notes

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