3-Hydroxypiperidine → HCID 60207438, compound

HRID 1192216Notes

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]([OH:20])=O)=[O:15])=[CH:11][C:10]=1[N+:21]([O-:23])=[O:22].[NH:25]1[CH2:30][CH2:29][CH2:28][CH:27]([OH:31])[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][CH2:28][CH:27]([OH:31])[CH2:26]2)=[O:20])=[O:15])=[CH:11][C:10]=1[N+:21]([O-:23])=[O:22]

Participants

Reactant 2

HCID 232933-Hydroxypiperidine

HCID 60207437HCID 60207437, compound

Product 1

HCID 60207438HCID 60207438, 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-3-ol (59.0 mg, 0.59 mmol). The title compound was obtained as a solid (25.0 mg, 11% yield). 1H NMR (400 MHz, d6-DMSO) δ: 9.04 (1H, m), 8.51 (1H, s), 4.87 (1H, m), 4.08 (2H, m), 3.58 (1H, m), 3.48 (1H, m), 3.38 (1H, m), 3.15 (1H, m), 2.60 (1H, m), 1.85 (1H, m), 1.75 (1H, m), 1.47 (1H, m), 1.33 (1H, m). MS m/z: 491.23, 493.26 [M+H]+.

Workup

customPrepared

Sources & evidence

ORD record: ord-3fce6221cb3b461981fc0d8e0e03e19e
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08680139B2

Reaction notes

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