Dimethylformamide → HCID 178472576, compound

HRID 516463Notes

Reaction equation

HRID 516463 reaction equation
[C:1]([C:4]1[CH:8]=[C:7]([C:9]([OH:11])=O)[NH:6][N:5]=1)(=[O:3])[CH3:2].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.CN(C=O)C.[CH2:50]([O:52][C:53](=[O:73])[C@H:54]([OH:72])[CH2:55][C@H:56]([NH2:71])[CH2:57][C:58]1[CH:63]=[CH:62][C:61]([C:64]2[CH:69]=[CH:68][CH:67]=[C:66]([Cl:70])[CH:65]=2)=[CH:60][CH:59]=1)[CH3:51]>C(Cl)Cl>[CH2:50]([O:52][C:53](=[O:73])[C@H:54]([OH:72])[CH2:55][C@H:56]([NH:71][C:9]([C:7]1[CH:8]=[C:4]([C:1](=[O:3])[CH3:2])[NH:5][N:6]=1)=[O:11])[CH2:57][C:58]1[CH:63]=[CH:62][C:61]([C:64]2[CH:69]=[CH:68][CH:67]=[C:66]([Cl:70])[CH:65]=2)=[CH:60][CH:59]=1)[CH3:51]

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 167673463-acetyl-1H-pyrazole-5-carboxylic acidHCID 86682253(2R,4R)-4-amino-5-(3'-chlorobiphenyl-4-yl)-2-hydroxypentanoic acid ethyl ester

Product 1

HCID 178472576HCID 178472576, compoundYield 13.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 3-acetyl-1H-pyrazole-5-carboxylic acid (50.9 mg, 330 μmol), HATU (125 mg, 330 μmol), and DIPEA (104 μL, 0.6 mmol) in DMF (0.6 mL, 7.7 mmol), was added (2R,4R)-4-amino-5-(3′-chlorobiphenyl-4-yl)-2-hydroxypentanoic acid ethyl ester (104 mg, 300 μmol). The resulting mixture was stirred at room temperature until the reaction was complete. The mixture was diluted with DCM and washed with saturated aqueous NaHCO3. The organics were dried over Na2SO4, and the solvent removed. Half of material was then purified by preparative HPLC to yield the title compound (20 mg) as a TFA salt. MS m/z [M+H]+ calc'd for C25H26ClN3O5, 484.16. found 484.1.

Workup

  1. washwashed with saturated aqueous NaHCO3
  2. dry with materialThe organics were dried over Na2SO4
  3. customthe solvent removed
  4. customHalf of material was then purified by preparative HPLC

Sources & evidence

ORD record
ord-329c99848252416b89b54a5b87da169e
Source dataset
uspto-grants-2015_08
Patent number
US09108934B2

Reaction notes

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