Ammonium Chloride → HCID 136366212, compound

HRID 1161476Notes

Reaction equation

HRID 1161476 reaction equation
C[N:2]([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.ON1C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.[Cl-].[NH4+].[F:49][C:50]([F:55])([F:54])[C:51]([OH:53])=[O:52].[C:56]([C:59]1[CH:64]=[CH:63][C:62]([NH:65][CH:66]([C:82]2[CH:87]=[CH:86][C:85]([O:88][CH2:89][C:90](=[O:94])[N:91]([CH3:93])[CH3:92])=[C:84]([O:95][CH3:96])[CH:83]=2)[C:67]2[NH:71][C:70](=[O:72])[N:69]([C:73]3[CH:81]=[CH:80][CH:79]=[CH:78][C:74]=3[C:75]([OH:77])=O)[N:68]=2)=[CH:61][CH:60]=1)(=[NH:58])[NH2:57]>CN(C=O)C>[F:49][C:50]([F:55])([F:54])[C:51]([OH:53])=[O:52].[C:56]([C:59]1[CH:64]=[CH:63][C:62]([NH:65][CH:66]([C:82]2[CH:87]=[CH:86][C:85]([O:88][CH2:89][C:90](=[O:94])[N:91]([CH3:93])[CH3:92])=[C:84]([O:95][CH3:96])[CH:83]=2)[C:67]2[NH:71][C:70](=[O:72])[N:69]([C:73]3[CH:81]=[CH:80][CH:79]=[CH:78][C:74]=3[C:75]([NH2:2])=[O:77])[N:68]=2)=[CH:61][CH:60]=1)(=[NH:58])[NH2:57]

Participants

7

Reactant 5

HCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 136366279HCID 136366279, compound

Product 1

HCID 136366212HCID 136366212, compoundYield 37.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

After adding 20.4 mg of BOP reagent, 5.3 mg of 1-hydroxybenzotriazole, 20.5 μl of N,N-diisopropylethylamine and 3.1 mg of ammonium chloride to a solution of 11.5 mg of 2-{3-[(4-carbamimidoyl-phenylamino)-(4-dimethylcarbamoylmethoxy-3-methoxy-phenyl)methyl]-5-oxo-4,5-dihydro-1H-[1,2,4]triazol-1-yl}benzoic acid trifluoroacetate in 1 ml of DMF, the mixture was stirred at room temperature for 22 hours. After filtering the reaction mixture, it was purified by reverse-phase high performance liquid chromatography (acetonitrile-water, 0.1% trifluoroacetic acid) to give 4.3 mg of the title compound.

Workup

  1. filtrationAfter filtering the reaction mixture, it
  2. customwas purified by reverse-phase high performance liquid chromatography (acetonitrile-water, 0.1% trifluoroacetic acid)

Sources & evidence

ORD record
ord-7a7a3e82d46e406d8ecdf4d4503f6779
Source dataset
uspto-grants-2010_10
Patent number
US07816522B2

Reaction notes

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