HCID 58169880, compound → HCID 58169900, compound

HRID 384027Notes

Reaction equation

HRID 384027 reaction equation
[F:1][C:2]([F:49])([F:48])[C:3]1[CH:4]=[C:5]([C@H:13]([N:15]([CH3:47])[C:16]([N:18]2[CH2:38][CH2:37][C@:21]3([N:25](C(OCC4C=CC=CC=4)=O)[C:24](=[O:36])[CH2:23][CH2:22]3)[CH2:20][C@@H:19]2[C:39]2[CH:44]=[CH:43][C:42]([F:45])=[CH:41][C:40]=2[CH3:46])=[O:17])[CH3:14])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1>CO.[Pd]>[F:49][C:2]([F:1])([F:48])[C:3]1[CH:4]=[C:5]([C@H:13]([N:15]([CH3:47])[C:16]([N:18]2[CH2:38][CH2:37][C@:21]3([NH:25][C:24](=[O:36])[CH2:23][CH2:22]3)[CH2:20][C@@H:19]2[C:39]2[CH:44]=[CH:43][C:42]([F:45])=[CH:41][C:40]=2[CH3:46])=[O:17])[CH3:14])[CH:6]=[C:7]([C:9]([F:10])([F:11])[F:12])[CH:8]=1

Participants

4

Reactant 1

HCID 58169880HCID 58169880, compound2×

Product 1

HCID 58169900HCID 58169900, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

phenylmethyl(5S,7R)-8-{[{(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethyl}(methyl)amino]carbonyl}-7-(4-fluoro-2-methylphenyl)-2-oxo-1,8-diazaspiro[4.5]decane-1-carboxylate (Intermediate 33 70 mg, 0.101 mmol) was dissolved in Methanol (3 ml) and to the solution was added Pd/C (10.74 mg, 10.09 μmol) The suspension was left stirring under H2 atmosphere for 30 mins. The palladium was filtered out and the solvent removed in vacuo obtaining the title compound (53.6 mg, 0.096 mmol, 95% yield); UPLC: Rt=0.81 mins, m/z=560 [M+H]+; MS: m/z=560 [M+H]+ and 582 [M+Na]+.

Workup

  1. waitwas left
  2. filtrationThe palladium was filtered out
  3. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-f07e89aef5f3403f92b50b60965c91b5
Source dataset
uspto-grants-2013_02
Patent number
US08367692B2

Reaction notes

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