4-Fluoropiperidine → HCID 60207442, compound

HRID 1192220Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:24])[C:7]=1[S:8][C:9]1[S:13][C:12]([C:14]([NH:16][CH2:17][C:18](O)=[O:19])=[O:15])=[CH:11][C:10]=1[N+:21]([O-:23])=[O:22].[F:25][CH:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1>>[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:24])[C:7]=1[S:8][C:9]1[S:13][C:12]([C:14]([NH:16][CH2:17][C:18]([N:29]2[CH2:30][CH2:31][CH:26]([F:25])[CH2:27][CH2:28]2)=[O:19])=[O:15])=[CH:11][C:10]=1[N+:21]([O-:23])=[O:22]

Participants

Reactant 2

HCID 27591594-Fluoropiperidine

HCID 60207437HCID 60207437, compound

Product 1

HCID 60207442HCID 60207442, compound

Procedure

Prepared according to the procedure described for example 70 from 2-(5-((3,5-dichloropyridin-4-yl)thio)-4-nitrothiophene-2-carboxamido)acetic acid (200 mg, 0.49 mmol) from example 210 and 4-fluoro-piperidine (60.0 mg, 0.59 mmol). The title compound was obtained as a solid (50.0 mg, 20% yield). 1H NMR (400 MHz, d6-DMSO) δ: 9.07 (1H, m), 8.98 (2H, m), 8.51 (1H, s), 4.93 (1H, m), 4.10 (2H, m), 3.54 (2H, m), 3.44 (2H, m), 1.92 (1H, m), 1.74 (2H, m), 1.61 (1H, m). MS m/z: 491.39, 493.37 [M+H]+.

Workup

customPrepared

Sources & evidence

ORD record: ord-94ab9a79dfd645a6a76336622a46399d
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08680139B2

Reaction notes

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