HCID 58169880, compound → HCID 58169900, compound

HRID 472695Notes

Reaction equation

HRID 472695 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-1a562ae3017b4113b3ae62db084d3560
Source dataset
uspto-grants-2014_01
Patent number
US08633214B2

Reaction notes

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