4-Piperidinemethanol → HCID 67494742, compound

HRID 1192231Notes

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].[NH:25]1[CH2:30][CH2:29][CH:28]([CH2:31][OH:32])[CH2:27][CH2:26]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:25]2[CH2:30][CH2:29][CH:28]([CH2:31][OH:32])[CH2:27][CH2:26]2)=[O:15])=[CH:11][C:10]=1[N+:21]([O-:23])=[O:22]

Participants

Reactant 2

HCID 4207714-Piperidinemethanol

HCID 60207450HCID 60207450, compound

Product 1

HCID 67494742HCID 67494742, 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 (150 mg, 0.37 mmol) and 4-piperidylmethanol (51.0 mg, 0.44 mmol). The title compound was afforded as a solid (30.0 mg, 17% yield). 1H NMR (400 MHz, d6-DMSO) δ: 8.98 (2H, m), 8.83 (1H, m), 8.40 (1H, s), 3.38 (1H, m), 3.21 (4H, m), 2.83 (2H, m), 2.28 (2H, m), 1.60 (4H, m), 1.30 (1H, m), 1.00 (2H, m). MS m/z: 503.33, 505.32 [M+H]+.

Workup

customPrepared

Sources & evidence

ORD record: ord-20f2df75ec094811b792757b0e63be69
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08680139B2

Reaction notes

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