HCID 86620142, compound → HCID 86620143, compound

HRID 1664922Notes

Reaction equation

HRID 1664922 reaction equation
[C:1]([N:4]1[CH2:10][C@H:9]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[C:12]=2[F:18])[CH2:8][CH2:7][C@@H:6]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH:5]1[C:27]#[N:28])(=[O:3])[CH3:2]>C(O)C.[Ni]>[C:1]([N:4]1[CH2:10][C@H:9]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[C:12]=2[F:18])[CH2:8][CH2:7][C@@H:6]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:23])([CH3:24])[CH3:25])[CH:5]1[CH2:27][NH2:28])(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 86620142HCID 86620142, compound

Product 1

HCID 86620143HCID 86620143, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

Raney-Nickel (2800, slurry in water; washed with ethyl alcohol (2×); 0.5 g) was added to a solution of tert-butyl [(3R,6S)-1-acetyl-2-cyano-6-(2,3-difluorophenyl)azepan-3-yl]carbamate (80.0 mg, 0.20 mmol) in ethanol (10 mL). Ammonia gas was bubbled to the reaction mixture for 3 minutes and the mixture was stirred under hydrogen at 40 psi. After 4 h, the reaction mixture was filtered and concentrated. MS 398.2 (M+1).

Workup

  1. customAmmonia gas was bubbled to the reaction mixture for 3 minutes
  2. filtrationthe reaction mixture was filtered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-86196788e4be468e9ae6f2d8f2523105
Source dataset
uspto-grants-2011_10
Patent number
US08039460B2

Reaction notes

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