Piperidine → HCID 25211188, compound

HRID 1409803Notes

Reaction equation

HRID 1409803 reaction equation
[F:1][CH:2]([F:17])[C:3]1[C:7]([CH3:8])=[C:6]([C:9]2[S:13][C:12]([C:14]([OH:16])=O)=[CH:11][CH:10]=2)[O:5][N:4]=1.[NH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1>>[F:17][CH:2]([F:1])[C:3]1[C:7]([CH3:8])=[C:6]([C:9]2[S:13][C:12]([C:14]([N:18]3[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]3)=[O:16])=[CH:11][CH:10]=2)[O:5][N:4]=1

Participants

3

Reactant 2

HCID 8082PiperidineHCID 25211001HCID 25211001, compound

Product 1

HCID 25211188HCID 25211188, compoundYield 72%

Procedure

Prepared from 5-(3-Difluoromethyl-4-methyl-isoxazol-5-yl)-thiophene-2-carboxylic acid (Preparative Example 27) 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 (110 mg, 72%). 1H NMR (CDCl3) 1.66-1.72 (6, 3 H), 2.35 (s, 3 H), 3.67-3.71 (m, 4 H), 6.79 (t, J=53.2, 1 H), 7.31 (d, J=4.0, 1 H), 7.45 (d, J=4.0, 1 H). 13C NMR 7.7, 24.7, 26.3, ˜46 (br), 39.8 (br), 108.7, 110.3 (t, J=236), 126.8, 128.8, 130.6, 140.6, 158.6 (q, J=30), 162.1, 162.5. 19F NMR −117.4 (J=53.5). LC/MS 6.36 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-0662f1b5ae794e9c81ffa2f8109a123a
Source dataset
uspto-grants-2014_12
Patent number
US08921399B2

Reaction notes

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