Piperidine → HCID 40012281, compound

HRID 1888412Notes

Reaction equation

HRID 1888412 reaction equation
[Br:1][C:2]1[S:6][CH:5]=[C:4]([C:7]([OH:9])=O)[CH:3]=1.CN(C(ON1N=N[C:20]2[CH:21]=[CH:22][CH:23]=[N:24][C:19]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.N1CCCCC1>C(#N)C.C(OCC)(=O)C>[Br:1][C:2]1[S:6][CH:5]=[C:4]([C:7]([N:24]2[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]2)=[O:9])[CH:3]=1

Participants

7

Reactant 4

HCID 8082PiperidineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 120399785-Bromothiophene-3-carboxylic acid

Product 1

HCID 40012281HCID 40012281, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-bromothiophene-3-carboxylic acid (1.03 g, 5.00 mmol) in acetonitrile (10 mL), were added HATU (2.09 g, 5.50 mmol), DIPEA (2.6 mL, 15.0 mmol) and piperidine (1.0 mL, 10.0 mmol) and the reaction mixture was stirred at room temperature for 24 h. The reaction mixture was diluted with ethyl acetate (75 mL) and was washed with saturated aqueous citric acid (2×50 mL). The organic layer was concentrated in vacuo and the resultant residue was loaded onto an SCX-2 cartridge. Eluting with acetonitrile and evaporation of the organic fraction in vacuo afforded the title compound as an off-white solid (1.00 g, 73%). LCMS (Method B): RT=3.3 min, M+H+=274.

Workup

  1. washwas washed with saturated aqueous citric acid (2×50 mL)
  2. concentrationThe organic layer was concentrated in vacuo
  3. washEluting with acetonitrile and evaporation of the organic fraction in vacuo

Sources & evidence

ORD record
ord-c66b71a9323a472da0ed7267dc9497aa
Source dataset
uspto-grants-2013_08
Patent number
US08501765B2

Reaction notes

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