Piperidine → HCID 25211187, compound

HRID 572279Notes

Reaction equation

HRID 572279 reaction equation
[F:1][CH:2]([F:17])[C:3]1[O:7][N:6]=[C:5]([C:8]2[S:12][C:11]([C:13]([OH:15])=O)=[CH:10][CH:9]=2)[C:4]=1[CH3:16].[NH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1>>[F:17][CH:2]([F:1])[C:3]1[O:7][N:6]=[C:5]([C:8]2[S:12][C:11]([C:13]([N:18]3[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]3)=[O:15])=[CH:10][CH:9]=2)[C:4]=1[CH3:16]

Participants

3

Reactant 2

HCID 8082PiperidineHCID 25210999HCID 25210999, compound

Product 1

HCID 25211187HCID 25211187, compoundYield 66%

Procedure

Prepared from 5-(5-Difluoromethyl-4-methyl-isoxazol-3-yl)-thiophene-2-carboxylic acid (Preparative Example 26) and piperidine by the method described in Example 2 Method B. The reaction mixture was evaporated in vacuo, then chromatographed on silica gel with EtOAc/hexanes (30 then 40%) as eluant to afford product as a colorless solid (54 mg, 66%). 1H NMR (CDCl3) 1.65-1.72 (6, 3H), 2.34 (s, 3H), 3.67-3.70 (m, 4H), 6.80 (t, J=53.2, 1H), 7.30 (d, J=4.0, 1H), 7.43 (d, J=3.5, 1H). 13C NMR 7.7, 24.7, 26.3, ˜46 (br), 39.8 (br), 108.1 (t, J=238), 113.5, 127.6, 128.9, 131.6, 140.1, 157.8, 159.5 (q, J=29), 162.7. 19F NMR −118.2 (J=53.5). LC/MS 6.18 min, [M+1]+ 327.

Workup

  1. customThe reaction mixture was evaporated in vacuo
  2. customchromatographed on silica gel with EtOAc/hexanes (30

Sources & evidence

ORD record
ord-53e14079abf944f2bb3c3e5b9f031f34
Source dataset
uspto-grants-2015_05
Patent number
US09029397B2

Reaction notes

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