Ethylmorpholine → HCID 60141144, compound

HRID 1854526Notes

Reaction equation

HRID 1854526 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:5]=[C:4]([C:13]([OH:15])=O)[CH:3]=1.[B-](F)(F)(F)F.CCOC(C(C#N)=NOC(N(C)C)=[N+](C)C)=O.C(N1CCOCC1)C.[NH2:46][C@H:47]([C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][C:53]=1[CH3:58])[CH2:48][C:49]([OH:51])=[O:50]>CN(C=O)C>[NH2:1][C:2]1[N:6]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:5]=[C:4]([C:13]([NH:46][C@H:47]([C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][C:53]=2[CH3:58])[CH2:48][C:49]([OH:51])=[O:50])=[O:15])[CH:3]=1

Participants

6

Reactant 4

HCID 7525EthylmorpholineHCID 2733286O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 6934180(3S)-3-Amino-3-(2-methylphenyl)propanoic acidHCID 233360985-Amino-1-phenyl-1H-pyrazole-3-carboxylic acid

Product 1

HCID 60141144HCID 60141144, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

100 mg (0.492 mmol) of 5-Amino-1-phenyl-1H-pyrazole-3-carboxylic acid are dissolved in 5 ml of DMF, 194 mg (0.59 mmol) of TOTU and 142 mg (1.23 mmol) of N-ethyl-morpholine is added. After stirring for 10 minutes at RT 97 mg (1.1 Eq, 0.54 mmol) of (S)-3-amino-3-(2-methyl-phenyl)-propionic acid are added and the resulting mixture is stirred overnight at RT. Solvent is removed in vacuo and the obtained crude product is submitted to HPLC chromatography: Yield: 32 mg, 18%

Workup

  1. additionare added
  2. customSolvent is removed in vacuo
  3. customthe obtained crude product

Sources & evidence

ORD record
ord-07f2f311edf14d9f87c6db4e4723606a
Source dataset
uspto-grants-2015_02
Patent number
US08962671B2

Reaction notes

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