Carbon Dioxide → HCID 59177792, compound

HRID 423625Notes

Reaction equation

HRID 423625 reaction equation
[F:1][C:2]1[CH:3]=[N:4][C:5]([N:8]2[CH2:13][CH2:12][CH:11]([CH:14]([O:16][C:17]3[CH:18]=[N:19][C:20]([C:23]4[CH:28]=[CH:27][C:26]([S:29]([CH3:32])(=[O:31])=[O:30])=[CH:25][CH:24]=4)=[CH:21][CH:22]=3)[CH3:15])[CH2:10][CH2:9]2)=[N:6][CH:7]=1.C(=O)=O>CO>[F:1][C:2]1[CH:7]=[N:6][C:5]([N:8]2[CH2:13][CH2:12][CH:11]([C@@H:14]([O:16][C:17]3[CH:18]=[N:19][C:20]([C:23]4[CH:24]=[CH:25][C:26]([S:29]([CH3:32])(=[O:31])=[O:30])=[CH:27][CH:28]=4)=[CH:21][CH:22]=3)[CH3:15])[CH2:10][CH2:9]2)=[N:4][CH:3]=1

Participants

4

Reactant 2

HCID 280Carbon DioxideHCID 59177748HCID 59177748, compound

Product 1

HCID 59177792HCID 59177792, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The racemic 5-fluoro-2-{4-[1-({6-[4-(methylsulfonyl)phenyl]-3-pyridinyl}oxy)ethyl]-1-piperidinyl}pyrimidine (prepared as in Example 153) was subjected to Chiral HPLC [column: OJ-H, column mobile phase: 70% CO2: 30% MeOH (2 mL/min), pressure 140 bar, temperature 40° C., 215 nm] analysis and then separated to give two (R and S) enantiomers. The title compound was isolated as an off-white solid with Tr of 21.34 min (first eluting peak). The (S) absolute stereochemistry was assigned by Ab initio VCD analysis.

Workup

  1. customseparated
  2. customto give two (R and S) enantiomers

Sources & evidence

ORD record
ord-4eb0f588f3b343e3b1864b7a6349f599
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Reaction notes

Loading…