HCID 136344401, compound → (5S,7R)-2-bromo-5-(1,3-dimethyl-1H-pyrazol-4-yl)-7-(trifluoromethyl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine

HRID 62223Notes

Reaction equation

HRID 62223 reaction equation
[Br:1][C:2]1[CH:21]=[C:5]2[NH:6][CH:7]([C:14]3[C:15]([CH3:20])=[N:16][N:17]([CH3:19])[CH:18]=3)[CH2:8][CH:9]([C:10]([F:13])([F:12])[F:11])[N:4]2[N:3]=1>CO>[Br:1][C:2]1[CH:21]=[C:5]2[NH:6][C@H:7]([C:14]3[C:15]([CH3:20])=[N:16][N:17]([CH3:19])[CH:18]=3)[CH2:8][C@H:9]([C:10]([F:11])([F:12])[F:13])[N:4]2[N:3]=1

Participants

3

Reactant 1

HCID 136344401HCID 136344401, compound

Product 1

HCID 136492809(5S,7R)-2-bromo-5-(1,3-dimethyl-1H-pyrazol-4-yl)-7-(trifluoromethyl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The racemic 2-bromo-5-(1,3-dimethyl-1H-pyrazol-4-yl)-7-(trifluoromethyl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine (1.5 g, 4.1 mmol, Preparation 8) was dissolved in methanol (35 mL) and the cloudy solution was gently warmed providing a clear solution. The solution was then filtered through a medium porosity Buchner funnel. The clear filtrate was directly used for chiral HPLC purification. 1 mL of this solution was loaded onto a 2.1 cm×25 cm Chiralcel OD column and eluted with a mobile phase comprising of isopropyl alcohol and methanol (1:1 ratio) at a flow rate of 15 mL/min. The two (R and S) enantiomers were collected separately. 27 such injections were carried out and the pooled fractions of pure (R and S) enantiomers were concentrated under reduced pressure. The title compound was isolated as a white powder (0.71 g, 1.95 mmols, >95% ee).

Workup

  1. temperaturethe cloudy solution was gently warmed
  2. customproviding a clear solution
  3. filtrationThe solution was then filtered through a medium porosity Buchner funnel
  4. customThe clear filtrate was directly used for chiral HPLC purification
  5. washeluted with a mobile phase comprising of isopropyl alcohol and methanol (1:1 ratio) at a flow rate of 15 mL/min
  6. customThe two (R and S) enantiomers were collected separately
  7. concentrationthe pooled fractions of pure (R and S) enantiomers were concentrated under reduced pressure

Sources & evidence

ORD record
ord-89f010a9190546d899398e67cb5addbb
Source dataset
uspto-grants-2016_09
Patent number
US09446046B2

Reaction notes

Loading…