4-Fluoropiperidine → HCID 67494778, compound

HRID 1192232Notes

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][CH2:18][CH:19]=O)=[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][CH2:18][CH2:19][N:29]2[CH2:30][CH2:31][CH:26]([F:25])[CH2:27][CH2:28]2)=[O:15])=[CH:11][C:10]=1[N+:21]([O-:23])=[O:22]

Participants

Reactant 2

HCID 27591594-Fluoropiperidine

HCID 60207450HCID 60207450, compound

Product 1

HCID 67494778HCID 67494778, compound

Procedure

Prepared according to the procedure described for step D of example 223 from 5-((3,5-dichloropyridin-4-yl)thio)-4-nitro-N-(3-oxopropyl)thiophene-2-carboxamide (130 mg, 0.32 mmol) and 4-fluoropiperidine (59.0 mg, 0.38 mmol). The title compound was afforded as a solid (15.0 mg, 10% yield). 1H NMR (400 MHz, d6-DMSO) δ: 8.98 (2H, m), 8.13 (1H, m), 8.41 (1H, s), 4.71 (1H, m), 3.32 (2H, m), 3.20 (2H, m), 2.27 (4H, m), 1.83 (2H, m), 1.65 (4H, m). MS m/z: 493.06, 495.05 [M+H]+.

Workup

customPrepared

Sources & evidence

ORD record: ord-1ebd6555629d435a8012091727be6a79
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08680139B2

Reaction notes

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