HCID 87319734, compound → HCID 67238817, compound

HRID 1470976Notes

Reaction equation

HRID 1470976 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C@H:10]2[CH2:14][CH2:13][C@H:12]([C:15]3[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[CH:17][CH:16]=3)[N:11]2[C:24]2[CH:29]=[CH:28][C:27]([N:30]3[CH2:35][CH2:34][O:33][CH2:32][CH2:31]3)=[CH:26][CH:25]=2)=[CH:6][CH:5]=1)([O-])=O.[H][H]>O1CCCC1.[Ni]>[O:33]1[CH2:34][CH2:35][N:30]([C:27]2[CH:28]=[CH:29][C:24]([N:11]3[C@@H:12]([C:15]4[CH:20]=[CH:19][C:18]([NH2:21])=[CH:17][CH:16]=4)[CH2:13][CH2:14][C@@H:10]3[C:7]3[CH:6]=[CH:5][C:4]([NH2:1])=[CH:9][CH:8]=3)=[CH:25][CH:26]=2)[CH2:31][CH2:32]1

Participants

5

Reactant 2

HCID 87319734HCID 87319734, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67238817HCID 67238817, compoundYield 44%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

The product from Example 98A in tetrahydrofuran (20 mL) was added to Ra-Ni (water wet, A-7000, 0.8 g, 12.63 mmol) in a 50 mL pressure bottle and stirred for 2 hours at ambient temperature under 30 psi of hydrogen. The mixture was filtered through a nylon membrane and concentrated to afford the title compound (0.31 g, 44%). MS (DCI) m/z 415 (M+H)+.

Workup

  1. filtrationThe mixture was filtered through a nylon membrane
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-1c8941065b5b49a384d3db0105a0d322
Source dataset
uspto-grants-2015_04
Patent number
US09006387B2

Reaction notes

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