HCID 178500494, compound → HCID 178500495, compound

HRID 1947271Notes

Reaction equation

HRID 1947271 reaction equation
[C:1]([C:3]1[CH:34]=[CH:33][C:6]([CH2:7][N:8]2[CH2:32][CH2:31][C:11]3([N:15]([CH2:16][CH2:17][CH2:18][C:19]([O:21][CH3:22])=[O:20])[C:14](=[O:23])[N:13]=[C:12]3[NH:24][CH:25]3[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]3)[CH2:10][CH2:9]2)=[CH:5][CH:4]=1)#[N:2]>[Ni].N>[NH2:2][CH2:1][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]2[CH2:32][CH2:31][C:11]3([N:15]([CH2:16][CH2:17][CH2:18][C:19]([O:21][CH3:22])=[O:20])[C:14](=[O:23])[N:13]=[C:12]3[NH:24][CH:25]3[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]3)[CH2:10][CH2:9]2)=[CH:33][CH:34]=1

Participants

4

Reactant 1

HCID 178500494HCID 178500494, compound

Product 1

HCID 178500495HCID 178500495, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalyst2×HCID 222AmmoniaSolvent

Procedure

Raney nickel (144 mg, 1.68 mmol, slurry in water) was placed under argon atmosphere. Methyl 4-[8-(4-cyanobenzyl)-4-(cyclohexylamino)-2-oxo-1,3,8-triazaspiro[4.5]dec-3-en-1-yl]butanoate (260 mg, 0.56 mmol) was dissolved in ammonia saturated methanol (5 mL) and added to Raney nickel solution. After 4 h at room temperature, full conversion was achieved and the slurry was filtered over celite, rinsing with ethanol. The filtrate was concentrated in vacuo to afford a yellow oil. LRMS (M+1)=470.5.

Workup

  1. filtrationthe slurry was filtered over celite
  2. washrinsing with ethanol
  3. concentrationThe filtrate was concentrated in vacuo
  4. customto afford a yellow oil

Sources & evidence

ORD record
ord-030bfdc242a34dc8bd424ef165283a66
Source dataset
uspto-grants-2013_03
Patent number
US08399473B2

Reaction notes

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