Potassium Carbonate → HCID 53251705, compound

HRID 1028094Notes

Reaction equation

HRID 1028094 reaction equation
C([O:4][CH2:5][C:6](=[O:30])[NH:7][C:8]1[S:9][C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([NH:19][C:20]3[N:25]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:23]=[CH:22][N:21]=3)[CH:14]=2)=[CH:11][N:12]=1)(=O)C.C(=O)([O-])[O-].[K+].[K+]>CO>[OH:4][CH2:5][C:6]([NH:7][C:8]1[S:9][C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([NH:19][C:20]3[N:25]=[C:24]([C:26]([F:27])([F:28])[F:29])[CH:23]=[CH:22][N:21]=3)[CH:14]=2)=[CH:11][N:12]=1)=[O:30]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 53251704HCID 53251704, compound

Product 1

HCID 53251705HCID 53251705, compoundYield 30.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 2-oxo-2-{[5-(3-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1,3-thiazol-2-yl]amino}ethyl acetate 1 (8.3 mg, 0.019 mmol) in MeOH (1 mL) at room temperature, under nitrogen, was added potassium carbonate (5.25 mg, 0.038 mmol). The mixture was stirred at room temperature for 18 hours. The mixture was filtered through celite and concentrated to dryness. The product was purified by column chromatography on silica gel (ethanol/ethyl acetatee) to afford 2-hydroxy-N-[5-(3-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1,3-thiazol-2-yl]acetamide (2.3 mg, 30.7%) as a beige solid. APCI [M+H]+ m/z 396.0. 1H NMR (400 MHz, DMSO): δ 11.86 (s, 1H); 10.31 (s, 1H); 8.86 (d, J=4.9 Hz, 1H); 8.12 (s, 1H); 7.82 (s, 1H); 7.65 (d, J=8.0 Hz, 1H); 7.42-7.23 (m, 3H); 5.55 (t, J=6.3 Hz, 1H); 4.18 (d, J=6.0 Hz, 2H). rhSYK activity=+++

Workup

  1. filtrationThe mixture was filtered through celite and
  2. concentrationconcentrated to dryness
  3. customThe product was purified by column chromatography on silica gel (ethanol/ethyl acetatee)

Sources & evidence

ORD record
ord-7534298387a34f85816b498766085623
Source dataset
uspto-grants-2014_05
Patent number
US08735417B2

Reaction notes

Loading…