Ethyl Acetate → HCID 58456412, compound

HRID 410505Notes

Reaction equation

HRID 410505 reaction equation
[BH4-].[Na+].[F:3][C:4]([F:32])([F:31])[C:5]([C:8]1[S:9][C:10]([C:13]2[CH:18]=[C:17]([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:16]=[C:15]([CH3:30])[CH:14]=2)=[CH:11][N:12]=1)(O)[OH:6].C(OCC)(=O)C.C([O-])(O)=O.[Na+]>CO>[F:31][C:4]([F:3])([F:32])[CH:5]([C:8]1[S:9][C:10]([C:13]2[CH:18]=[C:17]([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:16]=[C:15]([CH3:30])[CH:14]=2)=[CH:11][N:12]=1)[OH:6]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 86658248HCID 86658248, compound

Product 1

HCID 58456412HCID 58456412, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (41.6 mg, 1.099 mmol) was added to the product of Step 1 (450 mg, 0.999 mmol) in MeOH (3.3 mL) at 0° C. After stirring for 3 h, the reaction was poured into a separatory funnel containing ethyl acetate and saturated aqueous NaHCO3. The layers were separated and the organic layer was washed with water, brine, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by flash chromatography to give 2,2,2-trifluoro-1-[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1,3-thiazol-2-yl]ethanol (394.6 mg, 0.908 mmol, 91% yield) as a white solid. APCI: [M+H]+ m/z 435.1. 1H NMR (500 MHz, DMSO-d6) δ 10.28 (s, 1H), 8.84 (d, J=4.9, 1H), 8.12 (s, 1H), 8.02 (s, 1H), 7.86 (d, J=6.0, 1H), 7.48 (s, 1H), 7.29 (d, J=4.9, 1H), 7.22 (s, 1H), 5.52 (dd, J=6.7, 13.1, 1H), 2.32 (s, 3H). rhSYK activity=+++

Workup

  1. additionthe reaction was poured into a separatory funnel
  2. customThe layers were separated
  3. washthe organic layer was washed with water, brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-dfdeb65fa16b4bdf995bf8f9aa2eb674
Source dataset
uspto-grants-2014_06
Patent number
US08759366B2

Reaction notes

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