Diisopropylethylamine → N-{[3-(4-{[4-[5-Fluoro-2-(methyloxy)phenyl]-2-hydroxy-4-methyl-2-(trifluoromethyl)pentyl]amino}-6-methyl-1H-indazol-1-yl)phenyl]carbonyl}-N-methyl-L-alanine

HRID 1925584Notes

Reaction equation

HRID 1925584 reaction equation
[CH:1](N(CC)C(C)C)(C)C.[CH3:10][N:11]([C:13]([O:17]N1N=NC2C=CC=NC1=2)=[N+](C)C)[CH3:12].F[P-](F)(F)(F)(F)F.[F:34][C:35]1[CH:36]=[CH:37][C:38]([O:72][CH3:73])=[C:39]([C:41]([CH3:71])([CH3:70])[CH2:42][C:43]([OH:69])([C:65]([F:68])([F:67])[F:66])[CH2:44][NH:45][C:46]2[CH:54]=[C:53]([CH3:55])[CH:52]=[C:51]3[C:47]=2[CH:48]=[N:49][N:50]3[C:56]2[CH:57]=[C:58]([CH:62]=[CH:63][CH:64]=2)C(O)=O)[CH:40]=1.CN[C@H]([C:78]([OH:80])=[O:79])C>CN(C=O)C.CO.CS(C)=O>[F:34][C:35]1[CH:36]=[CH:37][C:38]([O:72][CH3:73])=[C:39]([C:41]([CH3:71])([CH3:70])[CH2:42][C:43]([OH:69])([C:65]([F:68])([F:67])[F:66])[CH2:44][NH:45][C:46]2[CH:54]=[C:53]([CH3:55])[CH:52]=[C:51]3[C:47]=2[CH:48]=[N:49][N:50]3[C:56]2[CH:57]=[C:58]([C:13]([N:11]([CH3:12])[C@H:10]([C:78]([OH:80])=[O:79])[CH3:1])=[O:17])[CH:62]=[CH:63][CH:64]=2)[CH:40]=1

Participants

8

Reactant 4

HCID 81531DiisopropylethylamineHCID 5288725N-Methyl-L-AlanineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 251807833-(4-{[4-[5-fluoro-2-(methyloxy)phenyl]-2-hydroxy-4-methyl-2-(trifluoromethyl)pentyl]amino}-6-methyl-1H-indazol-1-yl)benzoic acid

Product 1

HCID 57672635N-{[3-(4-{[4-[5-Fluoro-2-(methyloxy)phenyl]-2-hydroxy-4-methyl-2-(trifluoromethyl)pentyl]amino}-6-methyl-1H-indazol-1-yl)phenyl]carbonyl}-N-methyl-L-alanineYield 37.1%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

N,N-Diisopropylethylamine (0.149 mL, 0.855 mmol) and HATU (68.3 mg, 0.18 mmol) were added to a solution of 3-(4-{[4-[5-fluoro-2-(methyloxy)phenyl]-2-hydroxy-4-methyl-2-(trifluoromethyl)pentyl]amino}-6-methyl-1H-indazol-1-yl)benzoic acid (96 mg, 0.171 mmol) in DMF (1 mL) and the solution stirred at room temperature under nitrogen for 10 min. N-methyl-L-alanine (44.1 mg, 0.43 mmol) was added and the mixture stirred at room temperature for 5 days. The resulting suspension was diluted with methanol and DMSO to give a solution which was filtered and purified by mass directed autopreparation (System B) to give the title compound (40.9 mg).

Workup

  1. stirringthe mixture stirred at room temperature for 5 days
  2. customto give a solution which
  3. filtrationwas filtered
  4. custompurified by mass

Sources & evidence

ORD record
ord-839a147f64304f1e95e5462a0cde9efd
Source dataset
uspto-grants-2012_05
Patent number
US08178573B2

Reaction notes

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