Allylamine → HCID 86672813, compound

HRID 1519044Notes

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].[CH2:16]([NH2:19])[CH:17]=[CH2:18]>>[OH:1][C:2]1[C:7](=[O:8])[CH:6]=[CH:5][N:4]([CH3:9])[C:3]=1[CH:10]([NH:19][CH2:16][CH:17]=[CH2:18])[C:11]([F:14])([F:13])[F:12]

Participants

Reactant 2

HCID 7853Allylamine

HCID 67282261HCID 67282261, compound

Product 1

HCID 86672813HCID 86672813, compoundYield 42%

Procedure

In a similar manner, Apo7075 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 allylamine (0.67 mL, 9.0 mmol). The title compound Apo7075 (497 mg) was obtained after purification by flash chromatography (5% MeOH in CH2Cl2 as eluant). Yield=42%; 1H NMR (400 MHz, DMSO+a few drops of D2O) δ (ppm): 7.65 (d, J=7.1 Hz, 1H), 6.24 (d, J=7.4 Hz, 1H), 5.70-5.80 (m, 1H), 5.14 (d, J=17.4 Hz, 1H), 5.06 (d, J=10.1 Hz, 1H), 4.63 (q, J=8.2 Hz, 1H), 3.67 (s, 3H), 3.15-3.19 (m, 2H); MS m/z 263 [M+1]+, 206 (100%).

Sources & evidence

ORD record: ord-51efcd42e9884dc4b12559421afa9eb3
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09073865B2

Reaction notes

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