4-Pyridinemethanamine → HCID 22181338, compound

HRID 1796471Notes

Reaction equation

[CH2:1]([N:3]([CH2:16][CH3:17])[C:4](=[O:15])[C:5]1[CH:10]=[CH:9][C:8](F)=[C:7]([N+:12]([O-:14])=[O:13])[CH:6]=1)[CH3:2].[N:18]1[CH:23]=[CH:22][C:21]([CH2:24][NH2:25])=[CH:20][CH:19]=1>>[CH2:1]([N:3]([CH2:16][CH3:17])[C:4](=[O:15])[C:5]1[CH:10]=[CH:9][C:8]([NH:25][CH2:24][C:21]2[CH:22]=[CH:23][N:18]=[CH:19][CH:20]=2)=[C:7]([N+:12]([O-:14])=[O:13])[CH:6]=1)[CH3:2]

Participants

Reactant 2

HCID 773174-Pyridinemethanamine

HCID 22181444N,N-diethyl-4-fluoro-3-nitrobenzamide

Product 1

HCID 22181338HCID 22181338, compoundYield 60%

Procedure

Following general procedure 2B, N,N-diethyl-4-fluoro-3-nitrobenzamide (0.272 g, 1.13 mmol) and 4-pyridinylmethanamine (0.11 mL, 1.12 mmol) were stirred at room temperature for 87 h. The crude product was purified by column chromatography (100% EtOAc, then 9:1 CH2Cl2:MeOH) to provide the title compound (0.181 g, 60%). 1H-NMR (CD3OD): δ 8.49 (d, J=6.4 Hz, 2H), 8.27 (d, J=2.8 Hz, 1H), 7.50–7.42 (m, 3H), 6.87 (d, J=8.4 Hz, 1H), 4.77 (s, 2H), 3.44 (br s, 4H), 1.21 (t, J=7.2 Hz; 6H). MS (ESI) (M+H)+=329

Workup

customThe crude product was purified by column chromatography (100% EtOAc

Sources & evidence

ORD record: ord-7ab37e436cc943c3abac292fd73ee257
Source dataset: uspto-grants-2006_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07030139B2

Reaction notes

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