HCID 178482460, compound → HCID 178482458, compound

HRID 1510162Notes

Reaction equation

HRID 1510162 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:8]2[C@@:12]3([CH2:17][CH2:16][N:15](C(OCC4C=CC=CC=4)=O)[C@@H:14]([CH3:28])[CH2:13]3)[C:11]([NH:29][CH3:30])=[N:10][C:9]2=[O:31])[CH:5]=[CH:6][CH:7]=1>CO>[F:1][C:2]1[CH:3]=[C:4]([N:8]2[C@@:12]3([CH2:17][CH2:16][NH:15][C@@H:14]([CH3:28])[CH2:13]3)[C:11]([NH:29][CH3:30])=[N:10][C:9]2=[O:31])[CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 178482460HCID 178482460, compound2×

Product 1

HCID 178482458HCID 178482458, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The product from step 1 above, benzyl (5R,7S)-1-(3-fluorophenyl)-7-methyl-4-(methylamino)-2-oxo-1,3,8-triazaspiro[4.5]dec-3-ene-8-carboxylate (370 mg, 0.86 mmol) was dissolved in 8 mL MeOH. The solvent was degassed with a nitrogen flow for 10 min and Pd(OH)2 (30 mg, 20% wt. Pd) added. The mixture was purged with a hydrogen balloon for 10 min and then maintained under atmospheric hydrogen at rt overnight with stirring. The reaction was then filtered over Celite, the cake rinsed with EtOAc and the filtrate concentrated to dryness under reduced pressure to give after drying under vacuum the product as a white solid.

Workup

  1. customThe solvent was degassed with a nitrogen flow for 10 min
  2. additionPd(OH)2 (30 mg, 20% wt. Pd) added
  3. customThe mixture was purged with a hydrogen balloon for 10 min
  4. filtrationThe reaction was then filtered over Celite
  5. washthe cake rinsed with EtOAc
  6. concentrationthe filtrate concentrated to dryness under reduced pressure
  7. customto give
  8. dry with materialafter drying under vacuum the product as a white solid

Sources & evidence

ORD record
ord-2d41c56dec734b80a290faff15f2e548
Source dataset
uspto-grants-2012_07
Patent number
US08211904B2

Reaction notes

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