Phosphorus sulfide (P2S5) → HCID 75293434, compound

HRID 658943Notes

Reaction equation

HRID 658943 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]2[NH:8][C:9](=[O:41])[C:10]3([CH:15]([C:16]4[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:17]=4[O:23][C:24]([C:27]([O:29][CH3:30])=[O:28])([CH3:26])[CH3:25])[CH2:14][C:13](=O)[NH:12][CH:11]3[C:32]3[C:37]([F:38])=[C:36]([F:39])[CH:35]=[CH:34][C:33]=3[CH3:40])[C:5]2=[CH:4][CH:3]=1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:43]>C1COCC1.C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[C:6]2[NH:8][C:9](=[O:41])[C:10]3([CH:15]([C:16]4[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:17]=4[O:23][C:24]([C:27]([O:29][CH3:30])=[O:28])([CH3:26])[CH3:25])[CH2:14][C:13](=[S:43])[NH:12][CH:11]3[C:32]3[C:37]([F:38])=[C:36]([F:39])[CH:35]=[CH:34][C:33]=3[CH3:40])[C:5]2=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 14817Phosphorus sulfide (P2S5)HCID 72296181HCID 72296181, compound

Product 1

HCID 75293434HCID 75293434, compoundYield 91.6%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of racemic (2′S, 3S, 4′R)-6-chloro-4′-[5-chloro-2-(1-methoxycarbonyl-1-methyl-ethoxy)-phenyl]-2′-(5,6-difluoro-2-methyl-phenyl) spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione (40 mg, 0.067 mmol) and P2S5 (45 mg, 0.20 mmol) in THF (2 mL) was heated at 50° C. for 2 h, and then diluted with toluene (10 mL). The mixture was concentrated in vacuo and the residue was washed with DCM twice. The DCM layers were combined and concentrated. The residue was purified by flash chromatography to give the title compound as white solid (38 mg).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. washthe residue was washed with DCM twice
  3. concentrationconcentrated
  4. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-5374500b948f467bb277d26b5a16d69f
Source dataset
uspto-grants-2011_12
Patent number
US08076482B2

Reaction notes

Loading…