Benzoic Acid → N-Ethyl-N-(3,3,3-trifluoro-2-hydroxy-2-{[(1-phenyl-1H-indazol-4-yl)amino]methyl}propyl)benzamide

HRID 551437Notes

Reaction equation

HRID 551437 reaction equation
[C:1]([OH:9])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.[CH2:43]([NH:45][CH2:46][C:47]([CH2:53][NH:54][C:55]1[CH:63]=[CH:62][CH:61]=[C:60]2[C:56]=1[CH:57]=[N:58][N:59]2[C:64]1[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=1)([OH:52])[C:48]([F:51])([F:50])[F:49])[CH3:44]>CN(C=O)C.CS(C)=O>[CH2:43]([N:45]([CH2:46][C:47]([OH:52])([CH2:53][NH:54][C:55]1[CH:63]=[CH:62][CH:61]=[C:60]2[C:56]=1[CH:57]=[N:58][N:59]2[C:64]1[CH:65]=[CH:66][CH:67]=[CH:68][CH:69]=1)[C:48]([F:51])([F:50])[F:49])[C:1](=[O:9])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH3:44]

Participants

7

Reactant 4

HCID 243Benzoic AcidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 593241573-(Ethylamino)-1,1,1-trifluoro-2-{[(1-phenyl-1H-indazol-4-yl)amino]methyl}-2-propanol

Product 1

HCID 24769095N-Ethyl-N-(3,3,3-trifluoro-2-hydroxy-2-{[(1-phenyl-1H-indazol-4-yl)amino]methyl}propyl)benzamideYield 61.3%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6228DimethylformamideSolvent2×

Procedure

To benzoic acid (11 mg, 0.09 mmol) was added a solution of O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (34 mg, 0.09 mmol) in DMF (0.2 ml) followed by N,N-diisopropylethylamine (32 μL, 0.182 mmol). The mixture was shaken for 1 minute and then a solution of 3-(ethylamino)-1,1,1-trifluoro-2-{[(1-phenyl-1H-indazol-4-yl)amino]methyl}-2-propanol (26 mg, 0.07 mmol) in DMF (0.2 ml) was added. The mixture was again shaken for 1 minute and then left to stand at room temperature for 18 hours. The crude reaction was diluted with dimethyl sulfoxide (0.1 ml) and purified by mass-directed autopreparation (system A) to give the title compound (20.7 mg).

Workup

  1. stirringThe mixture was again shaken for 1 minute
  2. waitleft
  3. waitto stand at room temperature for 18 hours
  4. customThe crude reaction
  5. custompurified by mass-directed autopreparation (system A)

Sources & evidence

ORD record
ord-30460f9dbea8406ba8c6b148cc453fd0
Source dataset
uspto-grants-2011_05
Patent number
US07947727B2

Reaction notes

Loading…