Propanamide, 3,3,3-trifluoro-N-(4-mercaptophenyl)- → HCID 178428352, compound

HRID 499088Notes

Reaction equation

HRID 499088 reaction equation
[CH:1]1([C:4]2([F:26])[CH2:7][N:6]([C:8]3[N:13]=[C:12]([S:14]([CH3:17])(=O)=O)[N:11]=[C:10]([NH:18][C:19]4[NH:23][N:22]=[C:21]([CH3:24])[CH:20]=4)[C:9]=3[F:25])[CH2:5]2)[CH2:3][CH2:2]1.[F:27][C:28]([F:41])([F:40])[CH2:29][C:30]([NH:32][C:33]1[CH:38]=[CH:37]C(S)=[CH:35][CH:34]=1)=[O:31]>CN(C=O)C.C(OC(=O)C)C.C([O-])(O)=O.[Na+]>[CH3:24][C:21]1[CH:20]=[C:19]([NH:18][C:10]2[C:9]([F:25])=[C:8]([N:6]3[CH2:7][C:4]([CH:1]4[CH2:3][CH2:2]4)([F:26])[CH2:5]3)[N:13]=[C:12]([S:14][C:17]3[CH:35]=[CH:34][C:33]([NH:32][C:30](=[O:31])[CH2:29][C:28]([F:41])([F:27])[F:40])=[CH:38][CH:37]=3)[N:11]=2)[NH:23][N:22]=1

Participants

6

Reactant 2

HCID 57674932Propanamide, 3,3,3-trifluoro-N-(4-mercaptophenyl)-HCID 178428354HCID 178428354, compound

Product 1

HCID 178428352HCID 178428352, compoundYield 44.9%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A solution of 6-(3-cyclopropyl-3-fluoroazetidin-1-yl)-5-fluoro-N-(3-methyl-1H-pyrazol-5-yl)-2-(methylsulfonyl)pyrimidin-4-amine (64 mg, 0.17 mmol) and 3,3,3-trifluoro-N-(4-mercaptophenyl)propanamide (47 mg, 0.20 mmol) in DMF (3 ml) was heated to 80° C. and stirred for 6 hrs. The reaction was diluted with ethylacetate (20 ml) and Sat. NaHCO3 (20 ml) and the organic layer washed with brine (20 ml), dried (Na2SO4) and concentrated to give an oil. Compound was purified by mass directed preparative HPLC, eluted with acetonitrile/water/TFA to give the title compound as a white solid (TFA salt, 41.2 mg, 37%). 1H NMR (DMSO, 400 MHz) 0.46-0.50 (2H, m), 0.61-0.64 (2H, m), 1.38-1.45 (1H, m), 1.93 (3H, s), 3.55 (2H, q), 4.00-4.18 (4H, m), 5.27 (1H, s), 7.54 (2H, d), 7.71 (2H, d), 9.39 (1H, s), 10.57 (1H, s). ES+ 540.

Workup

  1. washthe organic layer washed with brine (20 ml)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. customto give an oil
  5. customCompound was purified by mass
  6. washeluted with acetonitrile/water/TFA

Sources & evidence

ORD record
ord-9dba89fc3e0346ac87aee0a4100a42d4
Source dataset
uspto-grants-2010_08
Patent number
US07767672B2

Reaction notes

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