Trifluoroacetic acid → HCID 136366199, compound

HRID 1161385Notes

Reaction equation

HRID 1161385 reaction equation
C(O)(=O)C.[OH:5][CH2:6][C:7]1[CH:8]=[C:9]([CH:15]([NH:28][C:29]2[CH:37]=[CH:36][C:32]([C:33]([NH2:35])=[NH:34])=[CH:31][CH:30]=2)[C:16]2[NH:20][C:19](=[O:21])[N:18]([C:22]3[N:27]=[CH:26][CH:25]=[CH:24][N:23]=3)[N:17]=2)[CH:10]=[C:11]([O:13][CH3:14])[CH:12]=1.[F:38][C:39]([F:44])([F:43])[C:40]([OH:42])=[O:41]>CS(C)=O>[F:38][C:39]([F:44])([F:43])[C:40]([OH:42])=[O:41].[OH:5][CH2:6][C:7]1[CH:8]=[C:9]([C@H:15]([NH:28][C:29]2[CH:30]=[CH:31][C:32]([C:33]([NH2:35])=[NH:34])=[CH:36][CH:37]=2)[C:16]2[NH:20][C:19](=[O:21])[N:18]([C:22]3[N:27]=[CH:26][CH:25]=[CH:24][N:23]=3)[N:17]=2)[CH:10]=[C:11]([O:13][CH3:14])[CH:12]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 136366244HCID 136366244, compound

Product 1

HCID 136366199HCID 136366199, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

After adding trifluoroacetic acid to a suspension of 28.5 mg of 4-{[(3-hydroxymethyl-5-methoxyphenyl)-(5-oxo-1-pyrimidin-2-yl-4,5-dihydro-1H-[1,2,4]triazol-3-yl)methyl]amino}benzamidine acetate in 2.85 ml of DMSO, the mixture was concentrated under reduced pressure. The residue was optically resolved using a SUMICHIRAL OA-2500 column, and the first eluting enantiomer was obtained. This was dissolved in a trifluoroacetic acid:acetonitrile:water=1:50:50 mixed solvent and concentrated, and the first eluting enantiomer (9.80 mg) of the title compound was obtained as a white solid.

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. customthe first eluting enantiomer was obtained
  3. concentrationacetonitrile:water=1:50:50 mixed solvent and concentrated

Sources & evidence

ORD record
ord-ed7e94c2a9b04d3d9268aa9ff1e22d38
Source dataset
uspto-grants-2010_10
Patent number
US07816522B2

Reaction notes

Loading…