Piperidine → HCID 70805181, compound

HRID 1519041Notes

Reaction equation

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

Participants

Reactant 2

HCID 8082Piperidine

HCID 67282261HCID 67282261, compound

Product 1

HCID 70805181HCID 70805181, compoundYield 54%

Procedure

In a similar manner, Apo7058 was prepared from 3-hydroxy-1-methyl-2-(2,2,2-trifluoro-1-hydroxyethyl)pyridin-4(1H)-one (1.0 g, 4.5 mmol) and piperidine (0.88 mL, 8.9 mmol). The title compound Apo7058 (700 mg) was obtained as a white solid after purification by flash chromatography (4% MeOH in CH2Cl2 as eluant). Yield=54%; 1H NMR (400 MHz, DMSO-D6, 75° C.) δ (ppm): 7.59 (d, J=6.8 Hz, 1H), 6.19 (d, J=6.8 Hz, 1H), 4.82 (q, J=9.0 Hz, 1H), 3.88 (s, 3H), 2.46-2.84 (m, 4H), 1.29-1.74 (m, 6H) MS m/z 291 [M+1]+, 206 (100%).

Sources & evidence

ORD record: ord-456c976037054aa48612857b093b3b3a
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09073865B2

Reaction notes

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