Triethylamine → HCID 58505374, compound

HRID 475446Notes

Reaction equation

HRID 475446 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][N:10]=1)[C:5]([OH:7])=O.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(CC)CC.FC(F)(F)C(O)=O.[CH:49]1([C@H:55]([NH:60][C:61]([C:63]2[O:64][C:65]([C:68]3[CH:73]=[CH:72][CH:71]=[C:70]([CH2:74][NH2:75])[CH:69]=3)=[CH:66][CH:67]=2)=[O:62])[C:56](=[O:59])[NH:57][CH3:58])[CH2:54][CH2:53][CH2:52][CH2:51][CH2:50]1>CN(C=O)C.C(OCC)(=O)C>[CH:49]1([C@H:55]([NH:60][C:61]([C:63]2[O:64][C:65]([C:68]3[CH:69]=[C:70]([CH:71]=[CH:72][CH:73]=3)[CH2:74][NH:75][C:5](=[O:7])[C:4]3[CH:8]=[CH:9][N:10]=[C:2]([F:1])[CH:3]=3)=[CH:66][CH:67]=2)=[O:62])[C:56](=[O:59])[NH:57][CH3:58])[CH2:54][CH2:53][CH2:52][CH2:51][CH2:50]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 3453602-Fluoroisonicotinic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86659069HCID 86659069, compound

Product 1

HCID 58505374HCID 58505374, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-fluoro-isonicotinic acid (22 mg, 0.16 mmol) in DMF (1 mL) is added HATU (61 mg, 0.16 mmol) and Et3N (0.044 mL, 0.3 mmol). After stirring at room temperature for 30 minutes, a solution of 5-(3-aminomethyl-phenyl)-furan-2-carboxylic acid ((S)-cyclohexyl-methylcarbamoyl-methyl)-amide trifluoroacetate salt (50 mg, 0.12 mmol) in DMF (1 mL) is added. The reaction is stirred for 2 hours, diluted with ethyl acetate and the organic layer washed with water and brine. The organic layer is evaporated in vacuo, and the resulting oil is purified by reverse phase HPLC to give the title compound as a solid, 21 mg, 41%, LC/MS ESI m/z (M+H)+493.5.

Workup

  1. stirringThe reaction is stirred for 2 hours
  2. washthe organic layer washed with water and brine
  3. customThe organic layer is evaporated in vacuo
  4. customthe resulting oil is purified by reverse phase HPLC

Sources & evidence

ORD record
ord-62be87aef7814989b7f9b8485ebe9a4f
Source dataset
uspto-grants-2014_01
Patent number
US08637550B2

Reaction notes

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