4-Piperidinemethanol → HCID 60207441, compound

HRID 1192219Notes

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].[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][C:18]([N:25]2[CH2:30][CH2:29][CH:28]([CH2:31][OH:32])[CH2:27][CH2:26]2)=[O:19])=[O:15])=[CH:11][C:10]=1[N+:21]([O-:23])=[O:22]

Participants

Reactant 2

HCID 4207714-Piperidinemethanol

HCID 60207437HCID 60207437, compound

Product 1

HCID 60207441HCID 60207441, 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 piperidin-4-ylmethanol (89.0 mg, 0.59 mmol). The title compound was obtained as a solid (25.0 mg, 8% yield). 1H NMR (400 MHz, d6-DMSO) δ: 9.02 (1H, m), 8.98 (1H, s), 8.50 (1H, s), 4.47 (1H, m), 4.32 (1H, m), 4.06 (2H, m), 3.83 (1H, m), 3.24 (2H, m), 2.96 (1H, m), 2.51 (1H, m), 1.66 (2H, m), 1.60 (1H, m), 1.11 (1H, m), 1.05 (1H, m), 0.92 (1H, m). MS m/z: 505.31, 507.27 [M+H]+.

Workup

customPrepared

Sources & evidence

ORD record: ord-78ec3f60af284386bb276306f471bd8e
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08680139B2

Reaction notes

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