Piperidine-1-propylamine → 6,7-dihydro-4-hydroxy-7-isobutyl-6-oxo-N-(3-(piperidin-1-yl)propyl)thieno[2,3-b]pyridine-5-carboxamide

HRID 1013879Notes

Reaction equation

[OH:1][C:2]1[C:3]2[CH:20]=[CH:19][S:18][C:4]=2[N:5]([CH2:14][CH:15]([CH3:17])[CH3:16])[C:6](=[O:13])[C:7]=1[C:8]([O:10]CC)=O.[N:21]1([CH2:27][CH2:28][CH2:29][NH2:30])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1>C1(C)C=CC=CC=1>[OH:1][C:2]1[C:3]2[CH:20]=[CH:19][S:18][C:4]=2[N:5]([CH2:14][CH:15]([CH3:16])[CH3:17])[C:6](=[O:13])[C:7]=1[C:8]([NH:30][CH2:29][CH2:28][CH2:27][N:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1)=[O:10]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of ethyl 6,7-dihydro-4-hydroxy-7-isobutyl-6-oxothieno[2,3-b]pyridine-5-carboxylate (0.1 g, 0.34 mmol), 3-(piperidin-1-yl)propan-1-amine (96 mg, 0.68 mmol) and toluene (15 mL) was heated at 100° C. for 2 h and cooled to room temperature. Solvent was removed under reduced pressure; the residue was purified on a silica gel flash chromatography column eluted with 3% methanol-dichloromethane to afford the title compound as a colorless oil (0.11 g, 83% yield). 1H NMR (400 MHz, CDCl3): δ 10.20 (br s, 1H), 7.38 (d, 1H), 6.95 (d, 1H), 3.92 (d, 2H), 3.49-3.44 (m, 2H), 2.90-2.78 (m, 6H), 2.40 (m, 1H), 2.20-1.38 (m, 8H), 1.00 (d, 6H); MS: m/e 392 (M+H+).

Workup

temperaturecooled to room temperature
customSolvent was removed under reduced pressure
customthe residue was purified on a silica gel flash chromatography column
washeluted with 3% methanol-dichloromethane

Sources & evidence

ORD record: ord-ee56120d197d4a378250814a7b66ee6b
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07982040B2

Reaction notes

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