Cyanoacetic acid → HCID 67971142, compound

HRID 1470749Notes

Reaction equation

HRID 1470749 reaction equation
[C:1]([CH2:3][C:4]([OH:6])=O)#[N:2].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[CH2:29]([O:31][C:32]1[CH:37]=[CH:36][C:35]([N:38]2[CH2:43][CH2:42][CH:41]([C:44]3[CH:49]=[CH:48][C:47]([C@@H:50]([NH2:52])[CH3:51])=[CH:46][CH:45]=3)[CH2:40][CH2:39]2)=[CH:34][CH:33]=1)[CH3:30]>CN(C=O)C>[C:1]([CH2:3][C:4]([NH:52][C@H:50]([C:47]1[CH:46]=[CH:45][C:44]([CH:41]2[CH2:40][CH2:39][N:38]([C:35]3[CH:34]=[CH:33][C:32]([O:31][CH2:29][CH3:30])=[CH:37][CH:36]=3)[CH2:43][CH2:42]2)=[CH:49][CH:48]=1)[CH3:51])=[O:6])#[N:2]

Participants

5

Reactant 3

HCID 9740Cyanoacetic acidHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 67125458HCID 67125458, compound

Product 1

HCID 67971142HCID 67971142, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To 7.0 mg (0.08 mmol) cyanoacetic acid in 1 mL DMF 35 μL (0.20 mmol) DIPEA and 29 mg (0.08 mmol) TBTU are added and the mixture is stirred for 10 min at rt. Subsequently 29 mg (0.09 mmol) (S)-1-{4-[1-(4-ethoxy-phenyl)-piperidin-4-yl]-phenyl}-ethylamine (XIII.1) in 1 mL DMF are added and stirring is continued over night. The mixture is filtered through basic aluminum oxide, followed by washing with DMF/MeOH (9:1) and concentration in vacuo. The residue is purified using reversed phase column chromatography (water/MeOH, 0.1% TFA) and the corresponding fractions are concentrated to yield the desired product.

Workup

  1. stirringstirring
  2. waitis continued over night
  3. filtrationThe mixture is filtered through basic aluminum oxide
  4. washby washing with DMF/MeOH (9:1) and concentration in vacuo
  5. customThe residue is purified
  6. concentrationthe corresponding fractions are concentrated

Sources & evidence

ORD record
ord-580faa7a606944998a98abb9b4aea4f6
Source dataset
uspto-grants-2015_04
Patent number
US09006450B2

Reaction notes

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