Piperidine → HCID 53308232, compound

HRID 1846677Notes

Reaction equation

HRID 1846677 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:18][C:19](=[O:27])[C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[CH:21]=2)[C:5]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][C:15]([OH:17])=O)[CH2:10][CH2:9]2)=[N:6][CH:7]=1.[NH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.C(N(CC)CC)C>CN(C)C=O>[Cl:26][C:22]1[CH:21]=[C:20]([CH:25]=[CH:24][CH:23]=1)[C:19]([NH:18][C:4]1[C:5]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][C:15](=[O:17])[N:28]3[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]3)[CH2:10][CH2:9]2)=[N:6][CH:7]=[C:2]([Cl:1])[CH:3]=1)=[O:27]

Participants

6

Reactant 4

HCID 8082PiperidineHCID 8471TriethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 67322178HCID 67322178, compound

Product 1

HCID 53308232HCID 53308232, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 0.011 g (0.027 mmol) of {4-[5-chloro-3-(3-chloro-benzoylamino)-pyridin-2-yl]-piperazin-1-yl}-acetic acid in N,N-dimethylformamide (1 mL), 0.011 g (0.13 mmol) of piperdine, 0.011 g (0.10 mmol) of O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate, and 0.011 mL (0.081 mmol) of triethylamine is stirred at room temperature for 4 hours. The mixture is concentrated under reduced pressure and the residue is diluted with water causing a solid to precipitate from solution. The material is collected by filtration, washed with water and dried on the filter pad to provide 0.0060 g (47%) of the title compound (282) as a colorless solid. [M+H]+=476.2.

Workup

  1. concentrationThe mixture is concentrated under reduced pressure
  2. additionthe residue is diluted with water causing a solid
  3. customto precipitate from solution
  4. filtrationThe material is collected by filtration
  5. washwashed with water
  6. customdried on the filter pad

Sources & evidence

ORD record
ord-3d6fea9291904e7b8c65bd1a1863c75d
Source dataset
uspto-grants-2015_02
Patent number
US08952004B2

Reaction notes

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