Dimethylformamide → (R)-3-[N'-(5-Acetyl-2H-pyrazole-3-carbonyl)-N-(5'-chloro-2'-fluorobiphenyl-4-ylmethyl)hydrazino]-2-hydroxypropionic Acid Ethyl Ester

HRID 541538Notes

Reaction equation

HRID 541538 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(=CC1=2)Cl)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN(C=O)C.CCN(C(C)C)C(C)C.[CH2:51]([O:53][C:54](=[O:75])[C@H:55]([OH:74])[CH2:56][N:57]([CH2:59][C:60]1[CH:65]=[CH:64][C:63]([C:66]2[CH:71]=[C:70]([Cl:72])[CH:69]=[CH:68][C:67]=2[F:73])=[CH:62][CH:61]=1)[NH2:58])[CH3:52]>>[CH2:51]([O:53][C:54](=[O:75])[C@H:55]([OH:74])[CH2:56][N:57]([CH2:59][C:60]1[CH:61]=[CH:62][C:63]([C:66]2[CH:71]=[C:70]([Cl:72])[CH:69]=[CH:68][C:67]=2[F:73])=[CH:64][CH:65]=1)[NH:58][C:9]([C:7]1[NH:6][N:5]=[C:4]([C:1](=[O:3])[CH3:2])[CH:8]=1)=[O:11])[CH3:52]

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 167673463-acetyl-1H-pyrazole-5-carboxylic acidHCID 42624899O-(6-Chlorobenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphateHCID 67972425(R)-3-[N-(5'-Chloro-2'-fluorobiphenyl-4-ylmethyl)hydrazino]-2-hydroxypropionic Acid Ethyl Ester

Product 1

HCID 86705114(R)-3-[N'-(5-Acetyl-2H-pyrazole-3-carbonyl)-N-(5'-chloro-2'-fluorobiphenyl-4-ylmethyl)hydrazino]-2-hydroxypropionic Acid Ethyl Ester

Procedure

3-Acetyl-1H-pyrazole-5-carboxylic acid (168 mg, 1.1 mmol) and HCTU (451 mg, 1.1 mmol) were combined in DMF (6.8 mL, 87.2 mmol), and stirred at room temperature. After 15 minutes, DIPEA (570 μL, 3.3 mmol) and (R)-3-[N-(5′-chloro-2′-fluorobiphenyl-4-ylmethyl)hydrazino]-2-hydroxypropionic acid ethyl ester (400 mg, 1.1 mmol) were added. The mixture was stirred for 20 minutes at room temperature, then evaporated under reduced pressure to yield the title compound. MS m/z [M+H]+ calc'd for C24H24ClFN4O5, 503.14. found 503.2.

Workup

  1. stirringThe mixture was stirred for 20 minutes at room temperature
  2. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-a03e7d5f23fc45b8a906ce56e40add54
Source dataset
uspto-grants-2014_10
Patent number
US08871792B2

Reaction notes

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