HCID 66818598, compound → HCID 66818168, compound

HRID 1024722Notes

Reaction equation

HRID 1024722 reaction equation
[C:1]([O:5][C:6](=[O:41])[NH:7][CH:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15](=[O:40])[C:16]2[CH:21]=[C:20]([O:22][C:23]3[CH:28]=[CH:27][C:26]([C:29]#[N:30])=[CH:25][CH:24]=3)[CH:19]=[C:18]([O:31][C:32]3[CH:37]=[CH:36][C:35]([C:38]#[N:39])=[CH:34][CH:33]=3)[CH:17]=2)[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2]>[Ni].N.CO>[C:1]([O:5][C:6](=[O:41])[NH:7][CH:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15](=[O:40])[C:16]2[CH:17]=[C:18]([O:31][C:32]3[CH:37]=[CH:36][C:35]([CH2:38][NH2:39])=[CH:34][CH:33]=3)[CH:19]=[C:20]([O:22][C:23]3[CH:28]=[CH:27][C:26]([CH2:29][NH2:30])=[CH:25][CH:24]=3)[CH:21]=2)[CH2:10][CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 66818598HCID 66818598, compound

Product 1

HCID 66818168HCID 66818168, compoundYield 82.6%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 21705897Ammonia methanolSolvent

Conditions

Temperature
50 °C

Procedure

0.05 g of Raney nickel was added to 0.3 g (0.54 mmol) of {4-[3,5-bis-(4-cyano-phenoxy)-benzoylamino]-cyclohexyl}-carbamic acid tert-butyl ester stirred with 50 ml of 10% NH3-methanol. The reaction mixture was stirred overnight on hydrogen gas pressure (50 psi) at 50° C. The reaction mixture was filtered through celite and concentrated to afford 0.25 g of the required product which was used for the next step without further purification. Percentage purity (LCMS): 70.8%, (M+1)=560.2+1

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-aad96541e7f44a63953f66e1263dddeb
Source dataset
uspto-grants-2014_05
Patent number
US08722930B2

Reaction notes

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