O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborate → HCID 178424252, compound

HRID 1183165Notes

Reaction equation

HRID 1183165 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]([OH:13])=[CH:11][C:10]([C:14]([OH:16])=O)=[N:9]1.[B-](F)(F)(F)F.CCOC(C(C#N)=NOC(N(C)C)=[N+](C)C)=O.[NH2:39][C@H:40]([C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][C:46]=1[CH3:51])[CH2:41][C:42]([OH:44])=[O:43]>CN(C=O)C>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]([OH:13])=[CH:11][C:10]([C:14]([NH:39][C@H:40]([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][C:46]=2[CH3:51])[CH2:41][C:42]([OH:44])=[O:43])=[O:16])=[N:9]1

Participants

5

Reactant 3

HCID 2733286O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 6934180(3S)-3-Amino-3-(2-methylphenyl)propanoic acidHCID 178524627HCID 178524627, compound

Product 1

HCID 178424252HCID 178424252, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.45 mmol of 1-(2-fluoro-phenyl)-5-hydroxy-1H-pyrazole-3-carboxylic acid were dissolved in 5 ml of DMF, 0.54 mmol of TOTU and 1.125 mmol of NEM were added, and the mixture was stirred for 5 min at room temperature. Then 0.495 mmol of (S)-3-amino-3-o-tolyl-propionic acid were added and the mixture stirred overnight at room temperature. The solvent was evaporated in vacuo and the residue subjected to preparative HPLC to give the title compound in a yield of 28%.

Workup

  1. stirringthe mixture stirred overnight at room temperature
  2. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-13f782e3cc9d408598720fb49799142c
Source dataset
uspto-grants-2014_03
Patent number
US08664257B2

Reaction notes

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