Ammonium Chloride → HCID 57736412, compound

HRID 1641744Notes

Reaction equation

HRID 1641744 reaction equation
[CH3:1][C:2]1[C:7]([CH:8]([S:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)(=[O:20])=[O:19])[C:9]2[C:14]([F:15])=[CH:13][CH:12]=[C:11]([F:16])[C:10]=2[F:17])=[CH:6][N:5]=[C:4]([C:27](O)=[O:28])[CH:3]=1.F[P-](F)(F)(F)(F)F.[N:37]1(O[P+](N2CCCC2)(N2CCCC2)N2CCCC2)C2C=CC=CC=2N=N1.N1(O)C2C=CC=CC=2N=N1.[Cl-].[NH4+].C(N(C(C)C)C(C)C)C>CN(C)C=O.O.C(OCC)(=O)C>[CH3:1][C:2]1[C:7]([CH:8]([S:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)(=[O:19])=[O:20])[C:9]2[C:14]([F:15])=[CH:13][CH:12]=[C:11]([F:16])[C:10]=2[F:17])=[CH:6][N:5]=[C:4]([C:27]([NH2:37])=[O:28])[CH:3]=1

Participants

9

Reactant 5

HCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 57736461HCID 57736461, compound

Product 1

HCID 57736412HCID 57736412, compoundYield 76.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-methyl-5-[(phenylsulfonyl)(2,3,6-trifluorophenyl)methyl]pyridine-2-carboxylic acid (300 mg, 0.71 mmol) in N,N-dimethylformamide (6 ml), (benzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate (556 mg, 1.07 mmol), benzotriazol-1-ol (144 mg, 1.07 mmol), ammonium chloride (76 mg, 1.42 mmol), and N-ethyldiisopropylamine (0.5 ml, 2.85 mmol) were added in an Argon atmosphere at room temperature. After stirring for 3 hours at room temperature, ethyl acetate and water were added to the reaction mixture, and the mixture was extracted with ethyl acetate, and then was washed with saturated brine. The organic layer was dried over anhydrous sodium sulfate and filtered, subsequently the filtrate was concentrated under reduced pressure, and the resulting residue was washed with diethyl ether, and then was collected by filtration, to obtain the title compound (227 mg, 0.54 mmol, 76%) as a white solid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washwas washed with saturated brine
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationsubsequently the filtrate was concentrated under reduced pressure
  6. washthe resulting residue was washed with diethyl ether
  7. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-d1ac3bd8eaaa4033b8908b2e17d35840
Source dataset
uspto-grants-2012_02
Patent number
US08114886B2

Reaction notes

Loading…