HCID 66816824, compound → HCID 66816362, compound

HRID 1754944Notes

Reaction equation

HRID 1754944 reaction equation
[OH:1][CH2:2][C@H:3]1[CH2:7][CH2:6][C:5](=[O:8])[N:4]1[C:9]1[CH:14]=[CH:13][C:12](/[CH:15]=[CH:16]/[S:17]([N:20]2[CH2:40][CH2:39][C:23]3([N:27]=[C:26]([C:28]4[CH:33]=[CH:32][CH:31]=[C:30]([C:34]([F:37])([F:36])[F:35])[CH:29]=4)[NH:25][C:24]3=[O:38])[CH2:22][CH2:21]2)(=[O:19])=[O:18])=[C:11]([CH3:41])[CH:10]=1.[H][H]>CCO.CN(C=O)C.[Pd]>[OH:1][CH2:2][C@H:3]1[CH2:7][CH2:6][C:5](=[O:8])[N:4]1[C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][S:17]([N:20]2[CH2:21][CH2:22][C:23]3([N:27]=[C:26]([C:28]4[CH:33]=[CH:32][CH:31]=[C:30]([C:34]([F:36])([F:35])[F:37])[CH:29]=4)[NH:25][C:24]3=[O:38])[CH2:39][CH2:40]2)(=[O:19])=[O:18])=[C:11]([CH3:41])[CH:10]=1

Participants

5

Reactant 2

HCID 66816824HCID 66816824, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 66816362HCID 66816362, compoundYield 45.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 19794673N,N-dimethylformamide ethanolSolvent

Procedure

8-{(E)-2-[4-((R)-2-Hydroxymethyl-5-oxo-pyrrolidin-1-yl)-2-methyl-phenyl]-ethenesulfonyl}-2-(3-trifluoromethyl-phenyl)-1,3,8-triaza-spiro[4.5]dec-1-en-4-one (28.5 mg, 48.3 μmol) was dissolved in EtOH/DMF 4:1 (concentration 10 mg/ml). The mixture was allowed to pass through 10% Pd/C (CatCart™) at a flow rate of 2 ml/min under the conditions of 30 bar and 40° C. in a hydrogen atmosphere, and was subjected to hydrogenation reaction. The resulting reaction solution was concentrated under reduced pressure. The residue was purified by preparative TLC(CH2Cl2/MeOH=20:1) to give 8-{2-[4-((R)-2-hydroxymethyl-5-oxo-pyrrolidin-1-yl)-2-methyl-phenyl]-ethanesulfonyl}-2-(3-trifluoromethyl-phenyl)-1,3,8-triaza-spiro[4.5]dec-1-en-4-one as a white powder (12.9 mg, 45%).

Workup

  1. customwas subjected to hydrogenation reaction
  2. customThe resulting reaction solution
  3. concentrationwas concentrated under reduced pressure
  4. customThe residue was purified by preparative TLC(CH2Cl2/MeOH=20:1)

Sources & evidence

ORD record
ord-3c59071688614c4b81d1783c7c4944a6
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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