Ammonium Chloride → HCID 59714851, compound

HRID 2223892Notes

Reaction equation

HRID 2223892 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]([CH:16]2[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][C:24]3([CH2:30][C:31]([OH:33])=O)[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]3)[CH2:18][CH2:17]2)[C:9]([C:11]2[O:12][CH:13]=[CH:14][CH:15]=2)=[O:10])=[N:6][CH:7]=1.[Cl-].[NH4+].F[P-](F)(F)(F)(F)F.[N:43]1(O[P+](N2CCCC2)(N2CCCC2)N2CCCC2)C2C=CC=CC=2N=N1.O.ON1C2C=CC=CC=2N=N1.C(=O)(O)[O-].[Na+]>CN(C)C=O>[C:31]([CH2:30][C:24]1([CH2:23][CH2:22][N:19]2[CH2:18][CH2:17][CH:16]([N:8]([C:5]3[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][N:6]=3)[C:9]([C:11]3[O:12][CH:13]=[CH:14][CH:15]=3)=[O:10])[CH2:21][CH2:20]2)[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]1)(=[O:33])[NH2:43]

Participants

7

Reactant 5

HCID 25517Ammonium ChlorideHCID 516892Sodium BicarbonateHCID 2724699PyBOPHCID 27960291-Hydroxybenzotriazole hydrateHCID 59714998HCID 59714998, compound

Product 1

HCID 59714851HCID 59714851, compoundYield 71.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

[1-[2-[4-[N-(5-Methylpyridin-2-yl)-2-furancarboxamido]piperidin-1-yl]ethyl]cyclohexyl]acetic acid (909 mg), ammonium chloride (216 mg), benzotriazol-1-yloxytrispyrrolidinophosphonium hexafluorophosphate (1.56 g), 1-hydroxybenzotriazole hydrate (470 mg) and N,N-diisoprpoylamine (1.4 mL) were dissolved in N,N-dimethylformamide (8 mL). The solution was stirred at room temperature for 22 hours. Saturated aqueous sodium bicarbonate solution was added to the solution, and it was extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate, filtered, and then, the solvent was distilled off under reduced pressure. The resulting residue was purified by chromatography (silica gel, chloroform:methanol=10:1) to give the title compound (652 mg).

Workup

  1. extractionwas extracted with chloroform
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe resulting residue was purified by chromatography (silica gel, chloroform:methanol=10:1)

Sources & evidence

ORD record
ord-3e73865b2e0248faa13c2097f874ef02
Source dataset
uspto-grants-2008_05
Patent number
US07375115B2

Reaction notes

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