Ammonium Chloride → HCID 57736492, compound

HRID 1641677Notes

Reaction equation

HRID 1641677 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH:9]([C:20]2[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:21]=2[F:27])[C:10]2[C:11]([CH3:19])=[CH:12][C:13]([C:16]([OH:18])=O)=[N:14][CH:15]=2)=[CH:4][CH:3]=1.F[P-](F)(F)(F)(F)F.[N:35]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.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8][CH:9]([C:20]2[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:21]=2[F:27])[C:10]2[C:11]([CH3:19])=[CH:12][C:13]([C:16]([NH2:35])=[O:18])=[N:14][CH:15]=2)=[CH:6][CH:7]=1

Participants

8

Reactant 5

HCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 57736463HCID 57736463, compound

Product 1

HCID 57736492HCID 57736492, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-[[(4-chlorophenyl)thio](2,5-difluorophenyl)methyl]-4-meth ylpyridine-2-carboxylic acid (406 mg, 1.00 mmol) in N,N-dimethylformamide (10 ml), (benzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate (781 mg, 1.50 mmol), 1-hydroxybenzotriazole (203 mg, 1.50 mmol), ammonium chloride (107 mg, 2.00 mmol), and N-ethyldiisopropylamine (0.697 ml, 4.00 mmol) were added in an argon atmosphere at room temperature. After stirring for 12 hours at room temperature, ethyl acetate was added to the reaction mixture, and the mixture was washed with 0.5 N hydrochloric acid. The organic layer was dried over anhydrous sodium sulfate and filtered, 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 (398 mg, 0.98 mmol, 98%) as a white solid.

Workup

  1. washthe mixture was washed with 0.5 N hydrochloric acid
  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-474da6dac57c41b6ae234ec21cc9afed
Source dataset
uspto-grants-2012_02
Patent number
US08114886B2

Reaction notes

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