Ammonium Chloride → HCID 66738671, compound

HRID 1641696Notes

Reaction equation

HRID 1641696 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[CH:9]([S:20][C:21]1[CH:22]=[N:23][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:25][CH:26]=1)[C:10]1[C:11]([CH3:19])=[CH:12][C:13]([C:16]([OH:18])=O)=[N:14][CH:15]=1.F[P-](F)(F)(F)(F)F.[N:38]1(O[P+](N2CCCC2)(N2CCCC2)N2CCCC2)C2C=CC=CC=2N=N1.ON1C2C=CC=CC=2N=N1.[Cl-].[NH4+].C(N(C(C)C)C(C)C)C>CN(C)C=O.O.C(OCC)(=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[CH:9]([S:20][C:21]1[CH:22]=[N:23][C:24]([C:27]([F:29])([F:28])[F:30])=[CH:25][CH:26]=1)[C:10]1[C:11]([CH3:19])=[CH:12][C:13]([C:16]([NH2:38])=[O:18])=[N:14][CH:15]=1

Participants

9

Reactant 5

HCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 57736501HCID 57736501, compound

Product 1

HCID 66738671HCID 66738671, compoundYield 96%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-[(2,5-difluorophenyl)[[6-(trifluoromethyl)pyridin-3-yl]thio]methyl]-4-methylpyridine-2-carboxylic acid (176 mg, 0.40 mmol) obtained in Example 26 in N,N-dimethylformamide (4 ml), (benzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate (312 mg, 0.60 mmol), 1-hydroxybenzotriazole (81 mg, 0.60 mmol), ammonium chloride (43 mg, 0.80 mmol), and N-ethyldiisopropylamine (0.279 ml, 1.60 mmol) were added in an argon atmosphere at room temperature. After stirring for 5 hours at room temperature, ethyl acetate and water were added to the reaction mixture, and the resulting mixture was washed with saturated brine. The organic layer was dried over anhydrous sodium sulfate and filtered, then the filtrate was concentrated under reduced pressure, and the resulting residue was subjected to flash silica gel chromatography. The fraction obtained from an elution with hexane:ethyl acetate=2:1 was concentrated under reduced pressure to obtain the title compound (168 mg, 0.38 mmol, 96%) as a white solid.

Workup

  1. washthe resulting mixture was washed with saturated brine
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe fraction obtained from an elution with hexane
  6. concentrationethyl acetate=2:1 was concentrated under reduced pressure

Sources & evidence

ORD record
ord-614fa079ffda4115a4d88e395aa7de65
Source dataset
uspto-grants-2012_02
Patent number
US08114886B2

Reaction notes

Loading…