Ammonium Chloride → HCID 22031350, compound

HRID 1792521Notes

Reaction equation

HRID 1792521 reaction equation
F[P-](F)(F)(F)(F)F.[N:8]1(O[P+](N2CCCC2)(N2CCCC2)N2CCCC2)C2C=CC=CC=2N=N1.O.ON1C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C.[Cl-].[NH4+].[N:56]1[CH:61]=[CH:60][CH:59]=[CH:58][C:57]=1[C:62]1[N:66]2[CH:67]=[C:68]([C:71]3[C:72]([C:95]4[CH:103]=[CH:102][C:98]([C:99]([OH:101])=O)=[CH:97][CH:96]=4)=[N:73][N:74]([C:76]([C:89]4[CH:94]=[CH:93][CH:92]=[CH:91][CH:90]=4)([C:83]4[CH:88]=[CH:87][CH:86]=[CH:85][CH:84]=4)[C:77]4[CH:82]=[CH:81][CH:80]=[CH:79][CH:78]=4)[CH:75]=3)[CH:69]=[CH:70][C:65]2=[N:64][CH:63]=1>O.C(OCC)(=O)C.CN(C)C=O>[N:56]1[CH:61]=[CH:60][CH:59]=[CH:58][C:57]=1[C:62]1[N:66]2[CH:67]=[C:68]([C:71]3[C:72]([C:95]4[CH:96]=[CH:97][C:98]([C:99]([NH2:8])=[O:101])=[CH:102][CH:103]=4)=[N:73][N:74]([C:76]([C:83]4[CH:84]=[CH:85][CH:86]=[CH:87][CH:88]=4)([C:89]4[CH:90]=[CH:91][CH:92]=[CH:93][CH:94]=4)[C:77]4[CH:78]=[CH:79][CH:80]=[CH:81][CH:82]=4)[CH:75]=3)[CH:69]=[CH:70][C:65]2=[N:64][CH:63]=1

Participants

9

Reactant 5

HCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 27960291-Hydroxybenzotriazole hydrateHCID 22031009HCID 22031009, compound

Product 1

HCID 22031350HCID 22031350, compoundYield 114.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

125 mg benzotriazol-1-yloxytripyrrolidinophosphonium hexafluorophosphate, 1-hydroxy-1H-benzotriazole monohydrate, 83 mg diisopropylethylamine, and 18 mg ammonium chloride were added in this order to a mixture of 100 mg 4-{4-[3-(2-pyridyl)imidazo[1,2-a]pyridin-6-yl]-1-trityl-1H-3-pyrazolyl} benzoic acid obtained in Example 46 and 3 mL N,N-dimethylformamide, and the mixture was stirred at room temperature for 2 hour. Ethyl acetate and water were added to the reaction solution, the organic layer was separated, the solvent was evaporated, and the residue was purified by NH silica gel column chromatography (hexane/ethyl acetate) to give 114 mg of the title compound as a colorless amorphous.

Workup

  1. customthe organic layer was separated
  2. customthe solvent was evaporated
  3. customthe residue was purified by NH silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-e731a84609504c2dbead9bf2573f28a6
Source dataset
uspto-grants-2006_07
Patent number
US07074801B1

Reaction notes

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