4-Fluorobenzoic Acid → HCID 68750889, compound

HRID 1864780Notes

Reaction equation

HRID 1864780 reaction equation
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:25][Si:26]([CH3:76])([CH3:75])[CH2:27][CH2:28][O:29][C:30]([N:32]1[CH2:37][CH2:36][CH:35]([NH:38][CH2:39][C:40]2[CH:45]=[C:44]([C:46]3[CH:73]=[CH:72][C:49]4[N:50]([C:53]([C:66]5[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=5)([C:60]5[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=5)[C:54]5[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=5)[N:51]=[N:52][C:48]=4[CH:47]=3)[CH:43]=[CH:42][C:41]=2[F:74])[CH2:34][CH2:33]1)=[O:31].[F:77][C:78]1[CH:86]=[CH:85][C:81]([C:82](O)=[O:83])=[CH:80][CH:79]=1.C(N(C(C)C)CC)(C)C>C(OCC)(=O)C>[CH3:25][Si:26]([CH3:76])([CH3:75])[CH2:27][CH2:28][O:29][C:30]([N:32]1[CH2:33][CH2:34][CH:35]([N:38]([C:82](=[O:83])[C:81]2[CH:85]=[CH:86][C:78]([F:77])=[CH:79][CH:80]=2)[CH2:39][C:40]2[CH:45]=[C:44]([C:46]3[CH:73]=[CH:72][C:49]4[N:50]([C:53]([C:54]5[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=5)([C:60]5[CH:61]=[CH:62][CH:63]=[CH:64][CH:65]=5)[C:66]5[CH:67]=[CH:68][CH:69]=[CH:70][CH:71]=5)[N:51]=[N:52][C:48]=4[CH:47]=3)[CH:43]=[CH:42][C:41]=2[F:74])[CH2:36][CH2:37]1)=[O:31]

Participants

6

Reactant 4

HCID 99734-Fluorobenzoic AcidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 68796575HCID 68796575, compound

Product 1

HCID 68750889HCID 68750889, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

HATU was added to a solution of 4-[2-fluoro-5-(1-trityl-1H-benzotriazol-5-yl)-benzylamino]-piperidine-1-carboxylic acid 2-trimethylsilany-1-ethyl ester, 4-fluorobenzoic acid and diisopropylethylamine and the resulting mixture stirred at ambient temperature overnight. The mixture was diluted with ethyl acetate washed with 1 M sodium carbonate solution. The layers were separated and the aqueous phase extracted with ethyl acetate. The combined organic phases were washed with brine, dried over magnesium sulfate, filtered and concentrated to leave the crude product. Chromatography (elution with diethyl ether/hexane, followed by ethyl acetate/hexane) provided 740 mg of product.

Workup

  1. washwashed with 1 M sodium carbonate solution
  2. customThe layers were separated
  3. extractionthe aqueous phase extracted with ethyl acetate
  4. washThe combined organic phases were washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto leave the crude product
  9. washChromatography (elution with diethyl ether/hexane, followed by ethyl acetate/hexane)

Sources & evidence

ORD record
ord-481533e7164544fc9cba62420738ac5e
Source dataset
uspto-grants-2009_12
Patent number
US07625889B2

Reaction notes

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