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Dimethylformamide → HCID 178472578, compound

HRID 516461
Notes
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Reaction equation

HRID 516461 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:74])[C@H:54]([OH:73])[CH2:55][C@H:56]([NH2:72])[CH2:57][C:58]1[CH:63]=[CH:62][C:61]([C:64]2[CH:69]=[C:68]([Cl:70])[CH:67]=[CH:66][C:65]=2[F:71])=[CH:60][CH:59]=1)[CH3:51]>C(Cl)Cl>[CH2:50]([O:52][C:53](=[O:74])[C@H:54]([OH:73])[CH2:55][C@H:56]([NH:72][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:59]=[CH:60][C:61]([C:64]2[CH:69]=[C:68]([Cl:70])[CH:67]=[CH:66][C:65]=2[F:71])=[CH:62][CH:63]=1)[CH3:51]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 86705150(2R,4R)-4-amino-5-(5'-chloro-2'-fluorobiphenyl-4-yl)-2-hydroxypentanoic acid ethyl ester

Product 1

HCID 178472578HCID 178472578, compoundYield 14.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 3-acetyl-1H-pyrazole-5-carboxylic acid (50.9 mg, 330 mol), 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-(5′-chloro-2′-fluorobiphenyl-4-yl)-2-hydroxypentanoic acid ethyl ester (110 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 (22 mg) as a TFA salt. MS m/z [M+H]+ calc'd for C25H25ClFN3O5, 502.15. found 502.1.

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-339ee0f73dd6476793ff765c435975d4
Source dataset
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09108934B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes