HCID 90414304, compound → US9434719, 334 as TFA salt

HRID 57493Notes

Reaction equation

HRID 57493 reaction equation
Cl[C:2]1[CH:3]=[C:4]([C@@H:14]([NH:16][C:17]2[N:22]=[C:21]([N:23]3[C@@H:27]([C@H:28]([OH:30])[CH3:29])[CH2:26][O:25][C:24]3=[O:31])[C:20]([F:32])=[CH:19][N:18]=2)[CH3:15])[CH:5]=[N:6][C:7]=1[O:8][CH2:9][C:10]([F:13])([F:12])[F:11]>CO.[OH-].[OH-].[Pd+2]>[F:32][C:20]1[C:21]([N:23]2[C@@H:27]([C@H:28]([OH:30])[CH3:29])[CH2:26][O:25][C:24]2=[O:31])=[N:22][C:17]([NH:16][C@H:14]([C:4]2[CH:5]=[N:6][C:7]([O:8][CH2:9][C:10]([F:12])([F:13])[F:11])=[CH:2][CH:3]=2)[CH3:15])=[N:18][CH:19]=1

Participants

4

Reactant 1

HCID 90414304HCID 90414304, compound

Product 1

HCID 90417127US9434719, 334 as TFA saltYield 80.2%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To (R)-3-(2-(((S)-1-(5-chloro-6-(2,2,2-trifluoroethoxyl)pyridin-3-yl)ethyl)amino)-5-fluoropyrimidin-4-yl)-4-((R)-1-hydroxyethyl)oxazolidin-2-one (20 mg, 0.042 mmol) in MeOH (10 mL) was added Pd(OH)2 (10 mg, 0.014 mmol). The reaction was purged with N2 and H2 three times each. A hydrogen balloon was applied to the reaction. The reaction mixture was stirred for one hour and concentrated. The residue was applied directly to HPLC separation to give product (15 mg) as a trifluoroacetic acid salt. 1HNMR (CD3OD) δ ppm 8.21 (d, J=3.1 Hz, 1H), 7.38 (t, J=8.0 Hz, 1H), 7.12-7.28 (m, 2H), 4.88-5.00 (m, 1H), 4.59 (br. s., 1H), 4.42-4.55 (m, 2H), 3.89 (br. s., 1H), 1.49 (d, J=7.0 Hz, 3H), 0.81 (br. s., 3H). HRMS (B) m/z 446.1448 (M+H)+, RT=1.90 min.

Workup

  1. customThe reaction was purged with N2 and H2 three times each
  2. customA hydrogen balloon was applied to the reaction
  3. concentrationconcentrated
  4. customThe residue was applied directly to HPLC separation

Sources & evidence

ORD record
ord-38ccca1f8c9e4b28bc5c3da26e85d8aa
Source dataset
uspto-grants-2016_09
Patent number
US09434719B2

Reaction notes

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