Piperidine-3-ol hydrochloride → (3-Hydroxy-piperidin-1-yl)-[5-(4-methyl-5-trifluoromethyl-isoxazol-3-yl)-thiophen-2-yl]-methanone

HRID 1514142Notes

Reaction equation

HRID 1514142 reaction equation
[F:1][C:2]([F:18])([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].Cl.[OH:20][CH:21]1[CH2:26][CH2:25][CH2:24][NH:23][CH2:22]1>>[OH:20][CH:21]1[CH2:26][CH2:25][CH2:24][N:23]([C:13]([C:11]2[S:12][C:8]([C:5]3[C:4]([CH3:16])=[C:3]([C:2]([F:1])([F:18])[F:17])[O:7][N:6]=3)=[CH:9][CH:10]=2)=[O:15])[CH2:22]1

Participants

3

Reactant 2

HCID 2723962Piperidine-3-ol hydrochlorideHCID 252109975-(4-Methyl-5-trifluoromethyl-isoxazol-3-yl)-thiophene-2-carboxylic acid

Product 1

HCID 57606120(3-Hydroxy-piperidin-1-yl)-[5-(4-methyl-5-trifluoromethyl-isoxazol-3-yl)-thiophen-2-yl]-methanone

Procedure

Prepared from 5-(5-trifluoromethyl-4-methyl-isoxazol-3-yl)-thiophene-2-carboxylic acid and (±)-3-hydroxypiperidine hydrochloride by the method described in Example 41. Colorless solid (101 mg, 85%). 1H NMR (CD3OD) 1.51-1.71 (m, 2H), 1.84-2.05 (m, 2H), 2.39 (q, JH-F=1.5, 3H), 3.34-3.65 (m, 2H), 3.68-3.85 (m, 2H), 3.86-4.14 (m, 1H), 7.49 (d, br, J=3.9, 1H), 7.60 (d, br, J=3.9, 1H). 13C NMR 8.0, 23.6 (br), 33.5, 45.1 (br), 55.1 (br), 67.0, 116.7 (q, J=2), 120.3 (q, J=270), 129.8, 130.9, 132.4, 141.1, 155.8 (q, J=40), 159.4, 165.0. 19F NMR −64.8. LC/MS 6.00 min, [M+1]+ 361.

Workup

  1. customLC/MS 6.00 min, [M+1]+ 361

Sources & evidence

ORD record
ord-10795884c24c419ea96d6c368cdcec95
Source dataset
uspto-grants-2012_07
Patent number
US08222243B2

Reaction notes

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