Piperidine → HCID 42643627, compound

HRID 1809086Notes

Reaction equation

HRID 1809086 reaction equation
[Cl:1][C:2]1[S:3][C:4]([CH2:10][CH3:11])=[CH:5][C:6]=1[C:7]([OH:9])=O.CCN(C(C)C)C(C)C.CN(C(ON1N=N[C:31]2[CH:32]=[CH:33][CH:34]=[N:35][C:30]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.N1CCCCC1>CN(C=O)C.C(#N)C.O>[Cl:1][C:2]1[S:3][C:4]([CH2:10][CH3:11])=[CH:5][C:6]=1[C:7]([N:35]1[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34]1)=[O:9]

Participants

8

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 59542561HCID 59542561, compound

Product 1

HCID 42643627HCID 42643627, compoundYield 42.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

2-Chloro-5-ethyl-thiophene-3-carboxylic acid (0.04 g, 0.21 mmol) was dissolved in DMF (6 mL). DIPEA (0.63 mmol), HATU (0.21 mmol) and piperidine (2.0 mmol) were added and the reaction stirred overnight. The mixture was diluted with acetonitrile and water and the product purified by HPLC, eluting with 20%-95% acetonitrile in water (0.1% formic acid) over 30 minutes. The fractions containing the desired product were concentrated under vacuum to give the title compound (0.023 g). LCMS m/z 358.08 [M+H]+RT=10.84 min (Analytical Method 2). 1H NMR (400 MHz, CHCl3-d): δ 6.6 (s, 1H), 3.7 (s, 2H), 3.35 (s, 2H), 2.75 (q, 2H), 1.6 (s, 6H), 1.3 (t, 3H).

Workup

  1. customthe product purified by HPLC
  2. washeluting with 20%-95% acetonitrile in water (0.1% formic acid) over 30 minutes
  3. additionThe fractions containing the desired product
  4. concentrationwere concentrated under vacuum

Sources & evidence

ORD record
ord-c74d3a3caa924cbca4385dc1639a83c9
Source dataset
uspto-grants-2013_01
Patent number
US08362008B2

Reaction notes

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