HCID 178519096, compound → HCID 178519143, compound

HRID 539102Notes

Reaction equation

HRID 539102 reaction equation
[NH:1]1[CH:5]=[N:4][C:3]([C:6]2[CH:11]=[CH:10][C:9]([C:12]3[CH:13]=[N:14][N:15]4[CH:20]=[CH:19][C:18]([N:21]5[CH:25]([C:26]6[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=6)[CH2:24][O:23][C:22]5=[O:32])=[N:17][C:16]=34)=[CH:8][CH:7]=2)=[N:2]1>C(O)C>[NH:1]1[CH:5]=[N:4][C:3]([C:6]2[CH:7]=[CH:8][C:9]([C:12]3[CH:13]=[N:14][N:15]4[CH:20]=[CH:19][C:18]([N:21]5[C@@H:25]([C:26]6[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=6)[CH2:24][O:23][C:22]5=[O:32])=[N:17][C:16]=34)=[CH:10][CH:11]=2)=[N:2]1

Participants

3

Reactant 1

HCID 178519096HCID 178519096, compound

Product 1

HCID 178519143HCID 178519143, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Racemic 3-(3-(4-(1H-1,2,4-triazol-3-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-(pyridin-2-yl)oxazolidin-2-one (Example 69) was dissolved in hot ethanol (10 mg/3 mL) and 1.5 ml, of the solution injected (8 injections total) onto a 2.2 cm×250 mm Chiral Tech OD-H column using 35% ethanol/65% hexanes as eluent with a 21 mL/minute flow rate. Peak 1 was isolated to provide (S)-3-(3-(4-(1H-1,2,4-triazol-3-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-(pyridin-2-yl)oxazolidin-2-one (19.2 mg). LCMS (APCI+) m/z 425 [M+H]+.

Workup

  1. customPeak 1 was isolated

Sources & evidence

ORD record
ord-f27968f5c1374d86b56918352a400894
Source dataset
uspto-grants-2014_10
Patent number
US08865726B2

Reaction notes

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