Ammonium Chloride → 4-{4-[5-(4-tert-Butylphenyl)-4-methyl-4H-[1,2,4]-triazol-3-ylsulfanyl]-2-heptyloxybenzyl amino}phenylacetamide

HRID 1171446Notes

Reaction equation

HRID 1171446 reaction equation
[N:1]1(O)C2C=CC=CC=2N=N1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C.[Cl-].[NH4+].[C:49]([C:53]1[CH:58]=[CH:57][C:56]([C:59]2[N:60]([CH3:91])[C:61]([S:64][C:65]3[CH:82]=[CH:81][C:68]([CH2:69][NH:70][C:71]4[CH:76]=[CH:75][C:74]([CH2:77][C:78](O)=[O:79])=[CH:73][CH:72]=4)=[C:67]([O:83][CH2:84][CH2:85][CH2:86][CH2:87][CH2:88][CH2:89][CH3:90])[CH:66]=3)=[N:62][N:63]=2)=[CH:55][CH:54]=1)([CH3:52])([CH3:51])[CH3:50]>CN(C)C=O.O>[C:49]([C:53]1[CH:58]=[CH:57][C:56]([C:59]2[N:60]([CH3:91])[C:61]([S:64][C:65]3[CH:82]=[CH:81][C:68]([CH2:69][NH:70][C:71]4[CH:76]=[CH:75][C:74]([CH2:77][C:78]([NH2:1])=[O:79])=[CH:73][CH:72]=4)=[C:67]([O:83][CH2:84][CH2:85][CH2:86][CH2:87][CH2:88][CH2:89][CH3:90])[CH:66]=3)=[N:62][N:63]=2)=[CH:55][CH:54]=1)([CH3:51])([CH3:50])[CH3:52]

Participants

8

Reactant 5

HCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 11157700(4-{4-[5-(4-tert-Butylphenyl)-4-methyl-4H-[1,2,4}-triazol-3-ylsulfanyl]-2-heptyloxybenzylamino}phenyl)acetic acid

Product 1

HCID 112272034-{4-[5-(4-tert-Butylphenyl)-4-methyl-4H-[1,2,4]-triazol-3-ylsulfanyl]-2-heptyloxybenzyl amino}phenylacetamideYield 66.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

152 mg (1.12 mmol, 1.5 eq) of benzotriazol-1-ol, 497 mg (1.12 mmol, 1.5 eq) of benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate, 780 μl (4.50 mmol, 4 eq) of diisopropylethylamine and finally 80 mg (1.50 mmol, 2 eq) of ammonium chloride are added to a solution of 450 mg (0.75 mmol, 1 eq) of (4-{4-[5-(4-tert-butylphenyl)-4-methyl-4H-[1,2,4]-triazol-3-ylsulfanyl]-2-heptyloxybenzyl amino}phenyl)acetic acid in 6 ml of dimethylformamide. The reaction mixture is stirred at room temperature for 24 hours, and then supplemented with a small amount of water. The precipitate obtained is filtered, dried and chromatographed on a silica gel cartridge (heptane/ethyl acetate 30/70). 298 mg (66%) of the expected compound are obtained.

Workup

  1. customThe precipitate obtained
  2. filtrationis filtered
  3. customdried
  4. customchromatographed on a silica gel cartridge (heptane/ethyl acetate 30/70)

Sources & evidence

ORD record
ord-e7aa38e8e5654c68a9b3e58e215c1d71
Source dataset
uspto-grants-2010_11
Patent number
US07829588B2

Reaction notes

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